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研究生: 雷姆希
Chintakunta Ramesh
論文名稱: 應用硝基苯類化合物為原料並經由分子內還原及環化反應來製備具有生物活性的含氮雜環化合物
Synthesis of Biologically Active N-Heterocycles via Intramolecular Reductive Cyclizations Of Nitroaromatics
指導教授: 姚清發
Yao, Ching-Fa
學位類別: 博士
Doctor
系所名稱: 化學系
Department of Chemistry
論文出版年: 2011
畢業學年度: 100
語文別: 英文
論文頁數: 315
中文關鍵詞: 還原環化貝里斯-希爾曼反應氮雜環鐵/醋酸硝基苯
英文關鍵詞: Reductive Cyclization, Baylis-Hillman Reaction, N-Heterocyles, Fe/AcOH, Nitroaromatics
論文種類: 學術論文
相關次數: 點閱:314下載:4
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  • 在有機化學合成領域的研究中,開發具有高效率和新穎的合成方式來合成含氮的雜環化合物是相當重要的,因為其具有廣泛的生物活性和在醫藥以及藥物化學領域的潛在應用性。在這個方面,以鄰位硝基芳香族化合物準備作為可行的起始物,藉由環化和還原反應來合成建構出多樣性的含氮原子之雜環分子。
    本論文主要分為四個章節。在第一章節,回顧有關於使用在醋酸中加入鐵粉以進行分子內環化和還原反應的相關文獻報導。在第二章節,主要是分為兩個部分,其中A部分是以新的合成方式,使用經過Baylis-Hillman reaction所得到的產物與indoles衍生物來進行碳-碳鍵的烷化反應,以合成出具有indole取代基的quinolines衍生物;B部分則是使用經過Baylis-Hillman reaction所得到的產物與indoles衍生物來進行碳-碳鍵的烷化和環化反應,以合成出具有indole取代基的吖啶以及indolylcyclopenta[b]quinoline的衍生物。在第三章節,主要是分為兩個部分,其中A部分是使用嶄新的合成路徑,在鐵粉/醋酸的條件下,使用3-(2-nitro-1-(2-nitrophenyl)ethyl)-1H-indoles來進行環化以及還原反應,合成出3,3'-biindoles之衍生物;B部分是使用簡潔的合成路徑,在鐵粉/醋酸的條件底下,合成出quinolines的衍生物。第四章節,同樣分為兩個部分,A部分是使用簡單和便利的合成路徑,在鐵粉/醋酸的條件底下,藉由2-(2-nitrophenoxy)acetonitrile經由環化和還原反應,合成出2H-1,4-benzoxazin-3-(4H)-ones的衍生物;B部分主要是使用具有高效率的“點擊”反應,藉由一價銅催化反應,將含有2H-1,4-benzoxazin-3-(4H)-one基團,合成出在1號位和4號位具有雙取代的1,2,3-三氮唑類衍生物。

    The development of efficient and novel protocols for the construction of N-heterocycles is fascinating and important area of research in synthetic organic chemistry due to their wide spectrum of biological activities and potential application in pharmaceutical field as well as in medicinal chemistry. In this respects, the o-nitro aromatics are readily available starting materials for the construction various nitrogen containing heterocyclic molecules via reductive cyclization.

    The contents of this dissertation is divided into four chapters, the Chapter I deals with overview on reductive cyclization and literature survey on intramolecular reductive cyclization in the presence of Fe powder in acetic acid. The Chapter II subdivided into two sections, section A deals with novel synthesis of indolylquinoline derivatives via the C-alkylation of Baylis-Hillman adducts and section B deals with novel synthesis of indolylacridines and indolylcyclopenta[b]quinoline derivatives from the C-alkylated cyclic Baylis-Hillman adducts. The Chapter III subdivided into two sections, section A deals with an unprecedented route for the synthesis of 3,3'-biindoles via reductive cyclization of 3-(2-nitro-1-(2-nitrophenyl)ethyl)-1H-indoles mediated by Fe/AcOH and Section B deals with Fe/AcOH mediated carbon degradation: a facile route for the synthesis of quinoline derivatives. The Chapter IV subdivided into two sections, section A deals with a simple and facile route for the synthesis of 2H-1,4-benzoxazin-3-(4H)-ones via reductive cyclization of 2-(2-nitrophenoxy)acetonitrile adducts in the presence of Fe/AcOH and section B deals with a highly efficient “ Click ” approach to synthesis of 1,4-disubstituted 1,2,3-triazole analogues containing 2H-1,4-benzoxazin-3-(4H)-one moiety via a copper (I)-catalyzed reaction.

    Abbreviations i-iv Abstract v-xiii Chapter-I : Overview on Reductive Cyclization I.1. Introduction 1 I.2. Fe/AcOH as Reductive Cyclizing agent 3 I.2.1. Reduction of aromatic nitro groups 4 I.2.2. Reduction of aliphatic nitro groups 13 I.3.References 15 Chapter-II, Section A: Novel synthesis of indolylquinoline derivatives via the C-alkylation of Baylis-Hillman adducts II.A.1. Introduction 20 II.A.2. Review of Literature 21 II.A.3. Results and Discussions 26 II.A.4. Conclusion 32 II.A.5. Experimental Section 33 II.A.6. References 43 Chapter-II, Section B: Application of the Baylis-Hillman Reaction: An Unprecedented in situ [1,3] sigmatropic rearrangement of indole nucleus to access novel indolylacridine and indolyl cyclopenta[b]quinoline derivatives II.B.1. Introduction 47 II.B.2. Review of Literature 48 II.B.3. Results and Discussions 50 II.B.4. Conclusion 60 II.B.5. Experimental Section 60 II.B.6. References 70 Chapter-III, Section A: An unprecedented route for the synthesis of 3,3'-biindoles via reductive cyclization of 3-(2-nitro-1-(2-nitrophenyl)ethyl)-1H-indoles mediated by Fe/AcOH III.A.1. Introduction 74 III.A.2. Review of Literature 75 III.A.3. Results and Discussions 78 III.A.4. Conclusion 83 III.A.5. Experimental Section 84 III.A.6. References 89 Chapter-III, Section B: Fe/AcOH mediated carbon degradation: a facile route for the synthesis of quinoline derivatives III.B.1. Introduction 92 III.B.2. Review of Literature 93 III.B.3. Results and Discussions 96 III.B.4. Conclusion 102 III.B.5. Experimental Section 102 III.B.6. References 108 Chapter-IV, Section A: A simple and facile route for the synthesis of 2H-1,4-benzoxazin-3-(4H)-ones via reductive cyclization of 2-(2-nitrophenoxy) aceto nitrile adducts in the presence of Fe/AcOH IV.A.1. Introduction 111 IV.A.2. Review of Literature 112 IV.A.3. Results and Discussions 114 IV.A.4. Conclusion 119 IV.A.5. Experimental Section 119 IV.A.6. References 128 Chapter-IV, Section B: A Highly Efficient “ Click ” Approach to Synthesis of 1,4-Disubstituted 1,2,3-Triazole analogues containing 2H-1, 4-benzoxazin-3-(4H)-one Moiety Via a Copper (I)-Catalyzed Reaction IV.B.1. Introduction 131 IV.B.2. Review of Literature 132 IV.B.3. Results and Discussions 133 IV.B.4. Conclusion 145 IV.B.5. Experimental Section 145 IV.B.6. References 158 X-Ray Crystallographic Data and NMR Spectra 162 List of Publications 315

    Chapter-I
    I.3.References
    1.(a) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875; (b) Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511; (c) Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447; (d) Tafesh, A. M.; Weiguny, J. Chem. Rev. 1996, 96, 2035.
    2.(a) Cruces, J.; Estevez, J. C.; Estevez, R. J.; Castedo, L. Heterocycles 2000, 53, 1041; (b) Suzuki, H.; Gyoutoku, H.; Yokoo, H.; Shinba, M.; Sato, Y.; Yamada, H.; Murakami, Y. Synth. Lett. 2000, 1196; (c) Hengartner, U.; Batcho, A. D.; Blount, J. F.; Leimgruber, M. E.; Larscheid, M. E.; Scott, J. W. J. Org. Chem. 1979, 44, 3748; (d) Reboredo, F. J.; Treus, M.; Este´vez, J. C.; Castedo, L.; Este´vez, R. J. Synth. Lett. 2002, 999; (e) Bunce, R. A.; Schammerhorn, J. E.; Slaughter, L. M. J. Heterocycl. Chem. 2007, 44, 1051; (f) Selvakumar, N.; Azhagan A. M.; Srinivas, D.; Krishna, G. G. Tetrahedron Lett. 2002, 43, 9175; (g) Bunce, R. A.; Nago, T.; Sonobe, N. J. Heterocycl. Chem. 2007, 44, 1059; (h) Dong, W.; Jimenez, L. S. J. Org. Chem. 1999, 64, 2520; (i) Chen, B.-C.; Hynes, Jr., J.; Randit, C. R.; Zhao, R.; Skoumbourdis, A. P.; Wu, H.; Sundeen, J. E.; Leftheris, K. Heterocycles 2001, 55, 951; (j) Wang, Z.; Jimenez, L. S. J. Org. Chem. 1996, 61, 816.
    3.Suzuki, H.; Gyoutoku, H.; Yokoo, H.; Shinba, M.; Sato, Y.; Yamada, H.; Murakami, Y. Synlett 2000, 1196.
    4.(a) Ruggli, P.; Dinger, A. Helv. Chim. Acta 1939, 22, 908; (b) Blair, J.; Newbold, G. T. J. Chem. Soc. 1955, 2871; (c) Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242.
    5.(a) Coutts, R. T.; Wibberley, D. G. J. Chem. Soc. 1962, 4610; (b) Macias, F. A.; Marin, D.; Bastidas, A. O.; Castellano, D.; Simonet, A. M.; Molinillo, J. M. G. J. Agric. Food Chem. 2005, 53, 538.
    6.Ohkubo, M.; Nishimura, T.; Jona, H.; Honma, T.; Morishima, H. Tetrahedron 1996, 52, 8009.
    7.Bentley, J. M.; Davidson, J. E.; Duncton, M. A. J.; Giles, P. R.; Pratt, R. M. Synth. Commun. 2004, 34, 2295.
    8.(a) Somei, M.; Inoue, S.; Tokutake, S.; Yamada, F.; Kaneko, C. Chem. Pharm. Bull. 1981, 29, 726; (b) Lee, K. Y.; Kim, S. C.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1109; (c) Mousseron-Canet, M.; Boca, J.-P. Bull. Soc. Chim. Fr. 1967, 1296; (d) Somei, M. Chem. Pharm. Bull. 1986, 34, 4109.
    9.(a) Piper, J. R.; Stevens, F. J. J. Heterocycl. Chem. 1966, 3, 95; (b) Zhichkin, P.; Kesicki, E.; Treiberg, J.; Bourdon, L.; Ronsheim, M.; Ooi, H. C.; White, S.; Judkins, A.; Fairfax, D. Org. Lett. 2007, 9, 1415; (c) Younes, E. A.; Husseina, A. Q.; May, M. A.; Fronczek, F. R. Arkivoc 2011, (ii), 322; (d) Lindwall, H. G.; Mantell, G. J. J. Org. Chem. 1953, 18, 345.
    10.a) Clark, C. I.; White, J. M.; Kelly, D. P.; Martin, R. F.; Lobachevsky, P. Aust. J. Chem. 1998, 51, 243; (b) Mamedov, V. A.; Saifina, D. F.; Gubaidullin, A. T.; Ganieva, V. R.; Kadyrova, S. F.; Rakov, D. V.; Rizvanov, d. K.; Sinyashin, O. G. Tetrahedron Lett. 2010, 51, 6503; (c) Novellino, L.; d'Ischia, M.; Prota, G. Synthesis 1999, 793; (d) Finger, G. C.; Gortatowski, M. J.; Shiley, R. H.; White, R. H. J. Am. Chem. Soc. 1959, 81, 94.
    11.Singh, V.; Kanojiya, S.; Batra, S. Tetrahedron 2006, 62, 10100.
    12.(a) Sandelier, M. J.; DeShong, P. Org. Lett. 2007, 9, 3209; (b) Dagommer, I.-G.; Gastaud, P.; RajanBabu, T. V. Org. Lett. 2011, 3, 2053.
    13.Muchowski, J. M.; Maddox, M. L. Can. J. Chem. 2004, 82, 461.
    14.(a) Guay, V.; Brassard, P. J. Heterocycl. Chem. 1987, 24, 1649; (b) Owsley, D. C.; Bloomfield, J. J. Synthesis 1977, 118; (c) Raucher, S.; Koolpe, G. A. J. Org. Chem. 1983, 48, 2066; (d) Hazlet, S. E.; Dornfeld, C. A. J. Am. Chem. Soc. 1944, 66, 1781; (d) Bunce, R. A.; Nammalwar, B. J. Heterocycl. Chem. 2011, 48, 991.
    15.Somei, M.; Kato, K.; Inoue, S. Chem. Pharm. Bull. 1980, 28, 2515.
    16.Clark, R. D.; Repke, D. B. Heterocycles 1984, 22, 195; (b) Rutherford, J. L.; Rainka, M. P.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 15168; (c) Hume, W. E.; Tokunaga, T.; Nagata, R. Tetrahedron 2002, 58, 3605; (d) Moody, C. J.; Rahimtoola, K. F. J. Chem. Soc. Perkin Trans. 1 1990, 673; (e) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673.
    17. Ma, Y.; Zhang, Y. J. Chem. Res. 2000, 388.
    18.(a) Lee, K. Y.; Lee, H. S.; Kim, J. N. Bull. Korean Chem. Soc. 2007, 28, 333; (b) Familoni, O. B.; Klaas, P. J.; Lobb, K. A.; Pakade, V. E.; Kaye, P. T. Org. Biomol. Chem. 2006, 4, 3960; (c) Lee, K. Y.; Kim, J. M.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 1493; (d) Singh, V.; Batra, S. Eur. J. Org. Chem. 2007, 2970; (e) Rosenmund, P.; Haase, W. H. Chem. Ber. 1966, 99, 2504; (e) Sharma, S.; Kundu, B. Tetrahedron Lett. 2008, 49, 7062; (f) McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257.
    19.Tafesh, A., unpublished results.
    20.Chen, H.; Nilsen, C, N.; Choudhury, A.; Sorgi, K. L. Arkivoc 2008, (Xiv), 1.
    21.(a) Bechamp, A. Ann. Chim. (Paris) 1854, 42, 180; (b) Bechamp, A. Justus Liebigs Ann. Chem. 1854, 92, 401; (c) Hamilton, C. S.; Morgan, J. F. Org. React. 1944, 2, 428; (d) Courtin, A. Helv. Chim. Acta. 1980, 62, 2280.
    22.(a) Agrawal, A.; Tratnyek, P. G. Environ. Sci. Technol. 1996, 30, 153; (b) Saha, A.; Ranu, B. J. Org. Chem. 2008, 73, 6867; (c) Pasha, M. A.; Jayashankara, V. P. Ultrason. Sonochem. 2005, 12, 433; (d) Zhou, Y.; Li, J.; Zhao, L.; Jiang, H. Tetrahedron Lett. 2006, 47, 8511; (e) Meng. X.; Cheng, H.; Fujita, S.-I.; Yu, Y.; Zhao, F.; Arai, M. Green Chem. 2011, 13, 570.
    23.Basavaiah, D.; Reddy, R. M.; Kumaragurubaran, N.; Sharada, D. S. Tetrahydron 2002, 58, 3693.
    24.Basavaiah, D.; Reddy, R. J.; Rao, J. S. Tetrahedron Lett. 2006, 47, 73.
    25.Basavaiah, D.; Rao, J. S.; Reddy, R. J. J. Org. Chem. 2004, 69, 379.
    26.Basavaiah, D.; Aravindu, K. Org. Lett. 2007, 9, 2453.
    27.Basaviah, D.; Reddy, K. R. Tetrahedron 2010, 66, 1215.
    28.Bunce, R. A.; Herron, D. M.; Ackerman M. L. J. Org.Chem. 2000, 65, 2847.
    29.Bunce, R. A.; Nammalwar, B.; Slaughter, L. M. J. Heterocycl. Chem. 2009, 46, 854.
    30.Bethuel, Y.; Gademann, K. J. Org. Chem. 2005, 70, 6258.
    31.Comesse, S.; Sanselme, M.; Daïch, A. J. Org. Chem. 2008, 73, 5566.
    32.Singh, V.; Hutait, S.; Batra, S. Eur. J. Org. Chem. 2009, 3454.
    33.Madapa, S.; Sridhar, D.; Yadav, G. P.; Maulik, P. R.; Batra, S. Eur. J. Org. Chem. 2007, 4343.
    34.Singh, V.; Singh, V.; Batra, S. Eur. J. Org. Chem. 2008, 5446.
    35.Mishra, A.; Batra, S. Eur. J. Org. Chem. 2010, 4832.
    36.Parvatkara, P. T.; P. S. Parameswarana, P. S.; Tilve, S. G. Tetrahedron Lett. 2007, 48, 7870.
    37.Santo, R. D.; Costi, R.; Forte, M.; Galeffi, C. Arkivoc 2004, (v), 181.
    38.(a) Mee, S. P. H.; Lee. V.; Baldwin, J. E.; Cowley, A. Tetrahedron 2004, 60, 3695; (b) Sinhahabu, A. K.; Borchardt, R. T. J. Org. Chem. 1983, 48, 3347.
    39.Jonsson, S.; Arribas, C. S.; Wendt, O. F.; Siegel, J. S.; Warnmark, K. Org. Biomol. Chem. 2005, 3, 996.
    40.Mishra, J. K.; Panda, G.; Synthesis 2005, 11, 1881.
    41.Reddy, D. J.; Kavala, V.; Bosco, J. W. J.; Kuo, C.-W.; Yao, C.-F. Eur. J. Org. Chem. 2011, 2360.
    42.Zhao, L.; Tao, K.; Li, H.; Zhang, J. Tetrahedron 2011, 67, 2803.
    43.Alonso, J.; Halland, N.; Nazaré, M.; R’kyek, O.; Urmann, M.; Lindenschmidt, A. Eur. J. Org. Chem. 2011, 234.
    44.Yong, S. R.; Ung, A. T.; Pyne, S. G.; Skelton, B. W.; White, A. H. Tetrahedron 2007, 63, 1191.
    45.Basavaiah, D.; Rao, J. S. Tetrahedron Lett. 2004, 45, 1621.
    46.Lee, M. J.; Lee, K. Y.; Park, D. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1281.
    47.Lee, H. S.; Kim, S. J.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 1063.
    48.Lee, K. Y.; Lee, Y. J.; Kim, J. N. Bull. Korean Chem. Soc. 2007, 28, 143.
    49.Yadav, L. D. S.; Rai, A. Synlett 2009, 7, 1067.
    Chapater-II, Section A:
    II.A.6. References
    1.(a) Michael, J. P. Nat. Prod. Rep. 1997, 14, 605; (b) Balasubramanian, M.; Keay, J. G. Comprehensive Hetero-cyclic Chemistry II Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Eds.; Pergamon: oxford, 1996; Vol 5, 245; (c) Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Blackwell Science: Oxford, 2000; p 121; (d) Sundberg, R. J. The Chemistry of Indoles; Academic: New York, 1996; p 113.
    2.Bhowal, S. K.; Lala S.; Hazra, A.; Paira, P.; Banerjee, S.; Mondal, N. B; Chakraborty, S. Contraception 2008, 77, 214.
    3.Ray, S.; Sadhukhan, P. K.; Mandal, N. B.; Mahato, S. B.; Majumder, H. K. Biochem &. Biophys. Res. Commun. 1997, 230, 171.
    4.Hoemann, M. Z.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. & Med. Chem. Lett. 2002, 12, 129.
    5.Cuny, G. D.; Hauske, J. R.; Hoemann, M. Z.; Chopra, I. US Patent 6376670, 2002, pp167.
    6.(a) Kuethe, J. T.; Wong, A.; Qu, C.; Smitrovich, J.; Davies, I. W.; Hughes, D. L. J. Org. Chem. 2005, 70, 2555; (b) Payack, J. F.; Vazquez, E.; Matty, L.; Kress, M. H.; McNamara, J. J. Org. Chem. 2005, 70, 175; (c) Wong, A.; Kuethe, J. T.; Davies, I. W.; Hughes, D. L. J. Org. Chem. 2004, 69, 7761; (d) Kuethe, J. T.; Wong, A.; Davies, I. W. Org. Lett. 2003, 5, 3975; (e) Fraley, M. E.; Arrington, K. L.; Buser, C. A.; Ciecko, P. A.; Coll, K. E.; Fernandes, C.; Hartman, G. D.; Hoffman, W. F.; Lynch, J. J.; McFall, R. C.; Rickert, K.; Singh, R.; Smith, S.; Thomas, K. A.; Wong, B. K. Bioorg. Med. Chem. Lett. 2004, 14, 351.
    7.Rickards, R. W.; Rothschild, J. M.; Willis, A. J.; de Chazal, N. M.; Kirk, J.; Kirk, K.; Saliba, K. J.; Smith, G. D. Tetrahedron 1999, 55, 13513.
    8.(a) Bernardo, P. H.; Chai, C. L. L.; Heath, G.A.; Mahon, P. J.; Smith, G. D.; Waring, P.; Wilkes, B. A. J. Med. Chem. 2004, 47, 4958; (b) Kaila, N.; Janz, K.; Huang, A.; Moretto, A.; DeBernardo, S.; Bedard, P. W.; Tam, S.; Clerin, V.; Keith, J. C. Jr.; Tsao, D. H. H.; Sushkova, N.; Shaw, G. D.; Camphausen, R. T. Schaub, R. G.; Wang, Q. J. Med. Chem. 2007, 50, 40; (c) Bernardo, P. H.; Chai, C. L. L. J. Org. Chem. 2003, 68, 8906; (d) Kelly,T. R.; Zhao, Y.; Cavero, M.; Torneiro, M. Org. Lett. 2000, 2, 3735.
    9.(a) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811; (b) Basavaiah, D.; Rao, K. V.; Reddy, R. J. Chem. Soc. Rev. 2007, 36, 1581.
    10.Familoni, O. B.; Kaye, P. T.; Klaas, P. J. Chem. Commun. 1998, 2563.
    11.(a) Kim, J. N.; Lee, K. Y.; Kim, H. S.; Kim, T. Y. Org. Lett. 2000, 2, 343; (b) Kim, J. N.; Lee, K. Y.; Ham, H.-S.; Kim, H. R.; Ryu, E. K. Bull. Korean Chem. Soc. 2001, 22, 135; (c) Chung, Y. M.; Lee, H. J.; Hwang, S. S.; Kim, J. N. Bull. Korean Chem. Soc. 2001, 22, 799; (d) Kim, J. N.; Lee, H. J.; Lee, K. Y.; Kim, H. S. Tetrahedron Lett. 2001, 42, 3737; (e) Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209; (f) O’Dell, D. K.; Nicholas, K. M. J. Org. Chem. 2003, 68, 6427; (g) Lee, K. Y.; Kim, S. C.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1109; (h) Kim, J. N.; Kim, H. S.; Gong, J. H.; Chung, Y. M. Tetrahedron Lett. 2001, 42, 8341; (i) Lee, K. Y.; Kim, J. M.; Kim, J. N. Tetrahedron 2003, 59, 385; (j) Basavaiah, D.; Reddy, R. M.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron 2002, 58, 3693; (k) Lee, K. Y.; Kim, J. M.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 1493; (l) Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 939; (m) Lee, C. G.; Lee, K. Y.; Gowri Sankar, S.; Kim, J. N. Tetrahedron Lett. 2004, 45, 7409; (n) Basavaiah, D.; Rao, J. S.; Reddy, R. J. J. Org. Chem. 2004, 69, 7379; (o) Lee, C. G.; Lee, K. Y.; Lee, S.; Kim, J. N. Tetrahedron 2005, 61, 1493; (p) Kim, S. C.; GowriSankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1001; (q) Narender, P.; Srinivas, U.; Ravinder, M.; Rao, B. A.; Ramesh, Ch.; Harakishore, K.; Gangadasu, B.; Murthy, U. S. N.; Rao, V. J. Bioorg. Med. Chem. 2006, 14, 4600; (r) Madapa, S.; Singh, V.; Batra, S. Tetrahedron 2006, 62, 8740; (s) Pathak, R.; Madapa, S.; Batra, S. Tetrahedron 2007, 63, 451; (t) Colacino E.; André, C.; Martinez, J.; Lamaty, F. Tetrahedron Lett. 2008, 49, 4953; (u) GowriSankar, S.; Lee, H. S.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2008, 49, 1670.
    12.(a) Ma. S.; Yu. S. Tetrahydron Lett. 2004, 45, 8419; (b) Ma. S.; Yu. S.; Peng. Z, Guo.H. J. Org. Chem. 2006, 71, 9865; (c) Ma. S.; Yu. S.; Peng. Z. Org. Biomol. Chem. 2005, 3, 1933; (d) Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narsaiah, A. V.; Prabhakar, A.; Jagadeesh. B. Tetrahedron Lett. 2005, 46, 639; (e) Yadav, J. S.; Reddy, B. V. S.; Singh, A. P.; Basak, A. K. Tetrahedron Lett. 2007, 48, 4169; (f) Nayak, M.; Pandey, G.; Batra. S. Tetrahedron 2011, 67, 7563; (g) Lee, H. S.; Kim, S. H.; Gowrisankar, S.; Kim, J. N. Tetrahedron 2008, 64, 7183.
    13.Mahato, S. B.; Mandal, N. B.; Chattopadhyaya, S.; Nandi, G.; Luger, P.; Weber, M. Tetrahedron 1994, 50, 10803.
    14.(a) Hamana, M.; Kumadaki, I. Chem. Pharm. Bull. 1967, 15, 363; (b) Yadav, J. S; Reddy, B. V. S.; Sathaiah, K.; Vishnumurthy, P. Synlett 2005, 18, 2811; (c) Hoemann, M. Z.; Badalian, A.-M.; G. Kumaravel, G.; Hauske, J. R. Tetrahedron Lett. 1998, 39, 4749; (d) Trofimov, B. A.; Nedolya, N. A.; Alan, R. K.; Christopher, A. R.; Eric, F. V. S.; Richard, J. K. T. in Comprehensive Heterocyclic Chemistry III, Elsevier, Oxford, 2008, p 45; (e) Yadav, J. S.; Reddy, B. V. S.; Yadav, N. N.; Gupta, M, K. Tetrahedron Lett. 2008, 49, 2815; (f) Birkinshaw, T. N.; Teague, S. J.; Beech, C.; Bonnert, R. V.; Hill. S.; Patel, A.; Reakes, S.; Sanganee, H.; Dougall, I.G.; Phillips, T. T.; Salter, S.; Schmidt, J.; Arrowsmith, E. C.; Carrillo, J. J.; Bell, F. M.; Pained, S. W.; Weaver, R. Bioorg. Med. Chem. Lett. 2006, 16, 4287; (g) Brasse, M.; Ellman, J. A.; Bergman, R. G. Chem. Commun. 2011, 47, 5019.
    15.(a) Payak, J.; Vazquez, E.; Matty, L.; Kress, M.; McNamara, J. J. Org. Chem. 2005, 70, 175; (b) Kuethe, J. T.; Wong, A.; Qu, Ch.; Smitrovich, J.; Davies, I. W.; Hughes, D. L. J. Org. Chem. 2005, 70, 2555; (c) Seregin, I.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
    16.(a) Zhu, S.; Ji, S.; Zhao, K.; Liu, Y. Tetrahedron Lett. 2008, 49, 2578; (b) Wong, A.; Kuethe, J. T.; Davies, I. W.; Hughes, D. L. J. Org. Chem. 2004, 69, 7761; (c) Kuethe, J.; Wong, A.; Davies, I. Org. Lett. 2003, 5, 3975.
    17.(a) Chu, C. M.; Gao, S. Sastry, M. N. V.; Yao, C.-F. Tetrahedron Lett. 2005, 46, 4971; (b) Ko, S. Sastry, M. N. V.; Lin, C.; Yao, C.-F. Tetrahedron Lett. 2005, 46, 5771; (c) Shivaji, V. M.; Sastry, M. N. V.; Wang, C. C.; Yao, C.-F. Tetrahedron Lett. 2005, 46, 6345; (d) Lin, C.; Hsu, J.; Sastry, M. N. V.; Fang, H.; Tu, Z.; Liu, J. T.; Yao, C.-F. Tetrahedron 2005, 61, 11751; (e) Ko, S.; Lin, C.; Tu, Z.; Wang, Y. F.; Wang, C. C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 487; (f) Gao, S.; Tzeng, T.; Sastry, M. N. V.; Chu, C. M.; Liu, J. T.; Lin, C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 1889; (g) Chu, C. M.; Huang, W. J.; Liu, J. J.; Yao, C.-F. Tetrahedron Lett. 2007, 48, 6881.
    18.(a) Basavaih, D.; Gowriswari, V. V. L. Tetrahedron Lett. 1986, 27, 2031; (b) Shi, M.; Jiang, J.-K.; Li, C.-Q. Tetrahedron Lett. 2002, 43, 127.
    19.Das, B.; Holla, H.; Srinivas, Y.; Chowdhury, N.; Bandgar, B. P. Tetrahedron Lett. 2007, 48, 3201.
    20.Nourry, A.; Legoupy, S.; Huet, F. Tetrahedron Lett. 2007, 48, 6014.
    Chapater-II, Section B:
    II.B.6. References

    1.(a) Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447; (b) Singh, V.; Batra, S. Tetrahydron 2008, 64, 4511; (c) Biswas, S.; Singh, V.; Batra, S. Tetrahydron 2010, 66, 7781; (d) Nag, S.; Bhowmik, S.; Gauniyal, H. M.; Batra, S. Eur. J. Org. Chem. 2010, 4705; (e) Mishra, A.; Batra, S. Eur. J. Org. Chem. 2010, 4832; (f) Basavaiah, D.; Lenin, D. V. Eur. J. Org. Chem. 2010, 5650; (g) Basavaiah, D.; Aravindu, K.; Kumar, K. S.; Reddy, K. R. Eur. J. Org. Chem. 2010, 1843; (h) Basavaiah, D.; Reddy, K. R. Tetrahedron 2010, 66, 1215; (i) Lei, J.; Cui, H.-L.; Li, R.; Wu, L.; Ding, Z.-Y.; Chen Y.-C. Org. Biomol. Chem. 2010, 8, 2840.
    2.(a) Chen, Y.-L.; Fang, K.-C.; Sheu, J.-Y.; Hsu, S.-L.; Tzeng, C.-C. J. Med. Chem. 2000, 44, 2374; (b) Roma, G.; Braccio, M. D.; Grossi, G.; Mattioli, F.; Ghia, H. Eur. J. Med. Chem. 2000, 35, 1021; (c) Chen, Y.-L.; Lu, C.-M.; Chen, I-L.; Tsao, L.-T.; Wang, J.-P. J. Med. Chem. 2002, 45, 4689; (d) Sánchez, I.; Reches, R.; Caignard, D. H.; Renard, P.; Pujol, M. D. Eur. J. Med. Chem. 2006, 41, 340; (e) Belmont, P.; Bosson, J.; Godet, T.; Tiano, M. Anticancer Agents Med. Chem. 2007, 7, 139; (f) Giorgio, C. D.; Shimi, K.; Boyer, G.; Delmas, F.; Galy, J.-P. Eur. J. Med. Chem. 2007, 42, 1277; (g) Mishra, V. K.; Bahel, S. C. J. Indian Chem. Soc. 1984, 61, 916; (h) Taraporewala, I. B.; Kauffman, J. M. J. Pharm. Sci. 1990, 79, 173; (i) Denny, W. A. Curr. Med. Chem. 2002, 9, 1655; (j) Antonin, I. Curr. Med. Chem. 2002, 9, 1701; (k) Wainwright, M. J. Antimicrob. Chemother. 2001, 47, 1.
    3.(a) Dictionary of Drugs, 1st ed.; Elks, J.; Ganellin, C. R. Eds.; Chapman and Hall: London, 1990; p 84; (b) Cain, B. F.; Atwell, G. J.; Denny, W. A. J. Med. Chem. 1975, 18, 1110.
    4.(a) Dictionary of Drugs, 1st ed.; Elks, J.; Ganellin, C. R. Eds.; Chapman and Hall: London, 1990; p 170; (b) Molnar, I.; Wagner-Jauregg, T.; Jahn, U.; U. S. Patent 3, 830, 918; Chem. Abstr. 1975, 83, 58674c.
    5.(a) Dictionary of Drugs, 1st ed.; Elks, J.; Ganellin, C. R. Eds.; Chapman and Hall: London, 1990; p 835; (b) Siegfried, A.-G. French Patent 1, 438, 357; Chem. Abstr. 1967, 66, 10856j.
    6.(a) Dictionary of Drugs, 1sted.; Elks, J.; Ganellin, C. R. Eds.; Chapman and Hall: London, 1990; p 297; (b) Zirkle, C. L. German Patent 1, 470, 245; Chem. Abstr. 1973, 78, 147825s.
    7.Gunawardana, G. P.; Kohmoto, S.; Gunasekara, S. P.; McConnell, O. J.; Koehn, F. E. J. Am. Chem. Soc. 1988, 110, 4856.
    8.Inman, W. D.; O’Neill-Johnson, M.; Crews, P. J. Am. Chem. Soc. 1990, 112, 1.
    9.(a) Magomedov, N. A. Org. Lett. 2003, 5, 2509; (b) Hubbs, J. L.; Heathcock, C. H. Org. Lett. 1999, 1, 1315.
    10.Gatta, F.; Del Giudice, M. R.; Pomponi, M.; Marta, M. Heterocycles. 1992, 34, 991.
    11.(a) Gamage, S. A.; Spicer, J. A.; Atwell, G. J.; Finlay, G. J.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 1999, 42, 2383; (b) Denny, W. A.; Cain, B. F.; Atwell, G. J.; Hansch, C.; Panthananickal, A.; Leo, A. J. Med. Chem. 1982, 25, 276; (c) Sondhi, S. M.; Singh, J.; Rani, R.; Gupta, P. P.; Agrawal, S. K.; Saxena, A. K. J. Med. Chem. 2010, 45, 555; (d) Baguley, B. C.; Denny, W. A.; Atwell, G.J.; Finlay, G. J.; Rewcastle, G. W.; Twigden, S. J. Wilson, W. R. Cancer Res. 1984, 44, 3245; (e) Antonini, I.; Polucci, P.; Magnano, A.; Sparapani, S.; Martelli, S. J. Med. Chem. 2004, 47, 5244; (f) Fadeyi, O. O.; Adamson, S. T.; Myles, E. L.; Okoro, C. O. Bioorg. Med. Chem. Lett. 2008, 18, 4172.
    12.(a) Dzierzbicka, K.; Kolodziejczyk. A. M. J. Med. Chem. 2001, 44, 3606; (b) Demeunynck, M.; Charmantray, A.; Martelli, A. Curr. Pharm. Des 2001, 7, 1703; (c) Kimura, M. J. Heterocycl.Chem. 1993, 30, 1101; (d) Isaev, S. G.; Shulga, I. S.; Kaliman, V. A.; Sheveleva, N. E.; Silaeva, L. F. Farm. Zh. (Kiev).1988, 2, 68.
    13.(a) Bentin, T.; Nielsen, P. E. J. Am. Chem. Soc. 2003, 125, 6378; (b) Lerman, L. S. J. Mol. Biol. 1961, 3, 18; (c) Kuruvilla, E.; Nandajan, P. C.; Schuster, G. B.; Ramaiah, D. Org. Lett. 2008, 10, 4295; (d) Joseph, J.; Kuruvilla, E.; Achuthan, A. T.; Ramaiah, D.; Schuster, G. B.; Bioconjug.Chem. 2004, 15, 1230.
    14.(a) Sanders, J. M.; Clifford, D. P.; Lutz, R. E.; J. Med. Chem. 1971, 14, 1126; (b) Lutz, R. E.; Sanders, J. M. J. Med.Chem. 1976, 19, 407.
    15.Burdi, N. Z. Biol. Deistvie Prod. Org. Sint. Prir. Soedin. 1978, 3-7; Chem. Abstr. 1979, 91, 151096r.
    16.(a) Upadysheva, A. V.; Grigor’eva, N. D.; Znamenskaya, A. P.; Sarkisyan, D. A.; Metkalova, S. E.; Antonyan, S. G.; Fleiderman, S. N.; Lavretskaya, E. F. Khim.-Farm.Zh. 1977, 11, 40; Chem. Abstr. 1977, 86, 189676q; (b) Hu, M.-K.; Wu, L.-J.; Hsiao, G.; Yen, M.-H. J. Med.Chem. 2002, 45, 2277.
    17.(a) Morita, K.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815; (b) Baylis, A. B.; Hillman, M. E. D. German Patent 2155113(1972); Chem. Abstr. 1972, 77, 34174q; (c) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811; (d) Basavaiah, D.; Dharmarao, P.; Hyma, R. S. Tetrahydron 1998, 44, 4653; (e) Ciganek, E.; In Organic Reactions; Paquette, L. A, Ed.; Wiley: New York, 1997; Vol. 51, p 201; (f) Masson, G.; Housseman, C.; Zhu, J. Angew. Chem. Int. Ed. 2007, 46, 4614; (g) Shi, Y. L.; Shi, M. Eur. J. Org. Chem. 2007, 2905.
    18.Familoni, O. B.; Kaye, P. T.; Klaas, P. J. Chem. Commun. 1998, 2563.
    19.(a) Basavaiah, D.; Reddy, R. J.; Rao, J. S.; Tetrahedron Lett. 2006, 47, 73; (b) Basavaiah, D.; Rao, A. J. Chem. Commun. 2003, 604; (c) Basavaiah, D.; Rao, J. S.; Reddy, R. J. J. Org. Chem. 2004, 69, 7379; (d) Rezgui, F.; Amri, H.; Gaïed, M. M. E. Tetrahedron 2003, 59, 1369; (e) Schwartz, B. D.; Tilly, D. P.; Heim, R.; Wiedemann, S.; Williams, C. M.; Bernhardt, P. V. Eur. J. Org. Chem. 2006, 3181; (f) Lee, K. Y.; Gowrisankar, S.; Lee, Y. J.; Kim, J. N. Tetrahedron Lett. 2005, 46, 5387; (g) Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627; (h) Shi, Y.-L.; Shi, M. Org. Biomol. Chem. 2007, 5, 1499.
    20.(a) Shafiq, Z.; Liu, L.; Wang, Z. L. D.; Chen, Y. J. Org. Lett. 2007, 9, 2525; (b) Shafiq, Z.; Qiao, Z.; Liu, L.; Zheng, Q. Y.; Wang, D.; Chen, Y. J. Synlett 2009, 18, 2965; (c) Basavaiah, D.; Rao, J. S.; Reddy, R. J. J. Org. Chem. 2004, 69, 7379; (d) Basavaiah, D.; Rao, A. J. Chem. Commun. 2003, 604; (e) Basavaiah, D.; Roy, S.; Das, U. Tetrahedron 2010, 66, 5612; (f) Shi, Y.-L.; Shi, M. Org. Biomol. Chem. 2007, 5, 1499; (g) Lee, K. Y.; Gowrisankar, S.; Lee, Y. J.; Kim, J. N. Tetrahedron Lett. 2005, 46, 5387; (h) Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627; (i) Schwartz, B. D.; Tilly, D. P.; Heim, R.; Wiedemann, S.; Williams, C. M.; Bernhardt, P. V. Eur. J. Org. Chem. 2006, 3181; (j) Singh, V.; Hutait, S.; Batra, S. Eur. J. Org. Chem. 2010, 3684; (k) Mishra, A.; Batra, S. Eur. J. Org. Chem. 2010, 4832.
    21.Qiao, Z.; Shafiq, Z.; Liu, L.; Yu, Z.-B.; Zheng, Q.-Y.; Wang, D.; Chen, Y.-J. Angew. Chem. Int. Ed. 2010, 49, 1.
    22.Ramesh, C.; Kavala, V.; Raju, B. R.; Kuo, C. W.; Yao, C.-F. Tetrahedron Lett. 2009, 50, 4037;
    23.Luo, S.; Wang, P. G.; Cheng, J.-P. J. Org. Chem. 2004, 69, 555.
    Chapter-III, Section A:
    III.A.6. References
    1.(a) Sundberg, R. J.; The Chemistry of Indoles; Academic Press: New York, 1996; p 113; (b) Joule, J. A.; In Science of Synthesis; E. J. Thomas, Ed.; Thieme: Stuttgart, 2000; Vol. 10, p 361; (c) Livingstone, R.; M. F. In Ansell, Ed.; Rodd’s Chemistry of Carbon Compounds; Elsevier: Oxford, 1984; Vol. 4; (d) Marugan, J. J.; Manthey, C.; Anaclerio, B.; Latrance, L.; Lu, T.; Markotan, T.; Leonard, K. A.; Crysler, C.; Eisennagel, S.; Dasgupta, M.; Tomczuk, B. J. Med. Chem. 2005, 48, 926; (e) Gribble, G. W.; J. Chem. Soc. Perkin Trans. 1 2000, 1045.
    2.(a) Lounasmaa, M.; Tolvanen, A.; Nat. Prod. Rep. 2000, 17, 175; b) Hibino, S.; Chozi, T. Nat. Prod. Rep. 2001, 18, 66; (c) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89; (d) Faul, M. M.; Winneroski, L. L.; Krumrich, C. A. J. Org. Chem. 1998, 63, 6053; (e) Bennasar, M.-L.; Vidal, B.; Bosch, J.; J. Org. Chem. 1997, 62, 3597; (f) Tani, M.; Matsumoto, S.; Aida, Y.; Arikawa, S.; Nakane, A.; Yokoyama, Y.; Murakami, Y. Chem. Pharm. Bull. 1994, 42, 443.
    3.(a) Gribble, G. W.; Berthel, S. J. Studies in Natural Products Chemistry; Ed. Atta-ur-Rahman. Elsevier: New York, 1993; Vol. 12, p 365; (b) Omura, S.; Sasaki, Y.; Iwai, Y.; Takeshita, H. J. Antibiot. 1995, 48, 535; (c) Pindur, U.; Kim, Y. S.; Mehrabani, F. Curr. Med. Chem. 1999, 6, 29; (d) d'Ischia, M.; Napolitano, A.; Pezzella, A.; Meredith, P.; Sarna, T. Angew. Chem. Int. Ed. 2009, 48, 2; (e) Ito, S.; Pigment Cell Res. 2003, 16, 230.
    4.(a) Bergman, J.; Janosik, T.; Wahlstrom, N. Adv. Heterocycl. Chem. 2001, 80, 1; (b) Pindur, U.; Kim, Y.-S.; Mehrabani, F. Curr. Med. Chem. 1999, 6, 29; (c) Bergman, J.; Stud. Nat. Prod. Chem. A 1988, 1, 3; (d) Gribble, G. W.; Berthel, S. J.; Stud. Nat. Prod. Chem. 1993, 12, 365; (e) Prudhomme, M.; Curr. Pharm. Design 1997, 3, 265.
    5.(a) Shi, D. Y.; Han, L. J.; Sun, J.; Li, S.; Wang, S. J.; Yang, Y. C.; Fan, X.; Shi, J. G. Chinese Chem. Lett. 2005, 16, 777; (b) Mee, S. P. H.; Lee, V.; Baldwin, J. E.; Cowle, A. Tetrahedron 2004, 60, 3695; (c) Hodder, A.; Capon, R. J. J. Nat. Prod. 1991, 54, 1661.
    6.Carter, M. D.; Hadden, M.; Weaver, D. F.; Jacobo, S. M. H. E. W.O. 2006/125324 A1
    7.Ohno, N. The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001.
    8.(a) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry, Vol. 2, Eds. Katritzky, A.; Rees, C. W.; Scriven, E. F. V. Pergamon, New York, 1996, p 119; (b) Clark, R. D.; Repke, D. B. Heterocycles 1984, 22, 195; (c) Ricci, A.; Fochi, M. Angew. Chem. Int. Ed. 2003, 42, 1444.
    9.(a) Suzuki, A.; In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J. Eds.;Wiley-VCH:Weinheim, Germany, 1998; Chapter 2, p 49; (b) Pezzella, A.; Panzella, L.; Natangelo, A.; Arzillo, M.; Napolitano, A.; d’Ischia, M. J. Org. Chem. 2007, 72, 9225; (c) Panzella, L.; Pezzella, A.; Napolitano, A.; d’Ischia, M. Org. Lett. 2007, 9, 1411; (d) d’Ischia, M.; Napolitano, A.; Pezzella, A.; Land, E. J.; Ramsden, C. A.; Riley, P. A. Adv. Heterocycl. Chem. 2005, 89, 1; (e) Kuethe, J. T.; Wong, A.; Davies, I. W. Org. Lett. 2003, 5, 3721; (f) Liang, Z.; Zhao, J.; Zhang, Y. J. Org. Chem. 2010, 75, 170 and references cited therein.
    10.(a) Kuethe, J. T.; Wong, A.; Davies, I. W. Org. Lett. 2003, 5, 3721; (b) Yepuri, N. R.; Haritakul, R.; Keller, P. A.; Skelton, B. W.; White, A. H. Tetrahedron Lett. 2009, 50, 2501; (c) Pelli, L.; Manini, P.; Pezzella, A.; Napolitano, A.; d ’ Ischia, M. J. Org. Chem. 2009, 74, 7191; (d) Keller, P. A.; Yepuri, N. R.; Kelso, M. J.; Mariani, M.; Skelton, B. W.; White, A. H. Tetrahedron 2008, 64, 7787; (e) Black, D. S. C.; Ivory, A. J.; Kumar, N. Tetrahedron 1996, 52, 7003; (f) Janosik, T.; Bergman, J. Tetrahedron 1999, 55, 2371.
    11.(a) Berens, U.; Brown, J. M.; Long, J.; Seike, R.; Tetrahedron: Asymmetry 1996, 7, 285; (b) Voldoire, A.; Sancelme, M.; Prudhomme, M.; Colson, P.; Houssier, C.; Bailly, C.; Léonce, S.; Lambel, S. Bioorg. Med. Chem. 2001, 9, 357; (c) Grigg, R.; Teasdale, A.; Sridharan, V. Tetrahedron Lett. 1991, 32, 3859; (d) Thomas, N. F.; Velu, S. S.; Weber, J.-F. F.; Lee, K. C.; Hadi, A. H. A.; Richomme, P.; Rondeau, D.; Noorbatchae, I.; Awanga, K. Tetrahedron 2004, 60, 11733; (e) Mee, S. P. H.; Lee, V.; Baldwin, J. E.; Cowley, A. Tetrahedron 2004, 60, 3695; (f) Li, Y.; Wang, W.-H.; Yang, S.-D.; Li, B.-J.; Feng, C.; Shi, Z.-J. Chem. Commun. 2010, 46, 4553; (g) Fujino, K.; Yanase, E.; Shinoda, Y.; Nakatsuka, S.-I. Biosci.Biotechnol.Biochem. 2004, 68, 764; (h) Bergman, J.; Eklund, N. Tetrahedron 1980, 36, 1445; (i) Desarbre, E.; Bergman, J. J. Chem. Soc. Perkin Trans. 1 1998, 2009.
    12.(a) Bartoli, G.; Bosco, M.; Giuli, S.; Giuliani, A.; Lucarelli, L.; Marcantoni, E.; Sambri, L.; Torregiani, E. J. Org. Chem. 2005, 70, 1941; (b) Lin, C.; Hsu, J.; Sastry, M. N. V.; Fang, H.; Tu, Z.; Liu, J.-T.; Yao, C.-F. Tetrahedron 2005, 61, 11751; (c) Ballini, R.; Clemente, R. R.; Palmieri, A.; Petrini, M. Adv. Synth. Catal. 2006, 348, 191; (d) Habib, P. M.; Kavala, V.; Kuo, C.-W.; Yao, C.-F. Tetrahedron Lett. 2008, 49, 7005; (e) An, L.-T.; Zou, J.-P.; Zhang, Y. Zhang, L. L. Tetrahedron Lett. 2007, 48, 4297; (f) Lin, S.-Z.; You, T.-P. Tetrahedron 2009, 65, 1010.
    13.(a) Wu, P.; Wan, Y.; Cai, J.; Synlett 2008, 1193; (b) Meshram, H. M.; Kumar, D. A.; Reddy, B. C. Helv. Chim. Acta 2009, 92, 1002; (c) Kuo, C.-W.; Wang, C.-C.; Fang, H.-L.; Raju, B. R.; Kavala, V.; Habib, P. M.; Yao, C.-F.; Molecules 2009, 14, 3952.
    14.An, L. T.; Zou, J. P.; Zhang, L. L.; Zhang, Y. Tetrahedron Lett. 2007, 48, 4297.
    15.(a) Chen, H.; Nilsen, C. N.; Choudhury, A.; Sorgi, K. L. Arkivoc 2008, (xiv), 1; (b) Owsley, D. C.; Bloomfield, J. J. Synthesis 1977, 2, 118.
    16.Singh, V.; Konojiya, S.; Batra, S. Tetrahedron 2006, 62, 10100.
    Chapter-III, Section B:
    III.B.6. References
    1.(a) Trost, B. M. Tamaru, Y. J. Am. Chem. Soc. 1977, 99, 3101; (b) Corbet, J.-P.; Banezra, C. Can. J. Chem. 1979, 57, 213; (c) Schteingart, C. D.; Hofmann, A. F. J. Lipid Res. 1988, 129, 1387; (d) Koskinen, A. M. P. ; Munoz, L. J. Chem. Soc., Chem. Commun. 1990, 1373; (e) Hoffmann, R. W.; Schlapbach, A. Tetrahedron Lett. 1993, 34, 7903; (f) Nagata, K.; Matsukawa, S.; Imamoto, T. J. Org. Chem. 2000, 65, 4185; (g) Markus, U.; Maier, M. E. Tetrahedron 2010, 66, 2633.
    2.(a) Hofmann, A. W. v. Ber. 1881, 14, 2725; (b) Mason, C. D.; Kord, F. F. J. Org. Chem. 1951, 16, 1869; (c) MacDonald, D. L.; Fischer, H.O. L. J. Am. Chem. Soc. 1952, 74, 2087; (d) Shioiri, T. Comp. Org. Syn. 1991, 6, 800; (e) Richter, L. S.; Andersen, S. Tetrahedron Lett. 1998, 39, 8747; (f) Hourdin, G.; Germain, A.; Moreau, C.; Fajula, F. J. Catal. 2002, 209, 217; (g) Dickstein, J. S.; Mulrooney, C. A.; O'Brien, E. M.; Morgan, B. J.; Kozlowski, M. C. Org. Lett. 2007, 9, 2441; (h) Stapley, J. A.; BeMiller, J. N. Carbohydrate Res. 2007, 342, 407; (i) Goossen, L. J.; Rodriguez, N.; Linder, C. J. Am. Chem. Soc. 2008, 130, 15248; (j) Lebreux, F.; Buzzo, F.; Markó, I. E. Synlett 2008, 2815; (k) Jana, R.; Trivedi, R.; Tunge, J. A. Org. Lett. 2009, 11, 3434; (l) Gao, S.; Tseng, C.; Raju, B. R.; Hsuan, C. T.; Yao, C.-F. Synlett 2009, 3201.
    3.(a) Belotti, D.; Andreatta, G.; Pradaux, F.; Bouz, S. B.; Cossy, J. Tetrahedron Lett. 2003, 44, 3613; (b) Taira, S.; Danjo, H.; Imamoto, T. Tetrahedron Lett. 2002, 43, 8893; (c) Itoh, K.; Ishida, H.; Chikashita, H. Chem. Lett. 1982, 1117.
    4.(a) Gildchrist, T. L. Six-membered Ring Compounds with One Heteroatom, 1st ed.; Pitman Publishing Ltd: London, 1985; (b) Lednicer, D.; Mitscher, L. A. The Organic Chemistry of Drug Synthesis; Wiley-Interscience: New York, 1977; Vol. 1, p 337; (c) Joshi, A. A.; Narkhede, S. S.; Viswanathan, C. L. Bioorg. Med. Chem. Lett. 2005, 15, 73; (d) Roma, G.; Di Braccio, M.; Grossi, G.; Mattioli, F.; Ghia, M. Eur. J. Med. Chem. 2000, 35, 1021; (e) Dube, D.; Blouin, M.; Brideau, C.; Chan, C. C.; Desmarais, S.; Ethier, D.; Falgueyret, J. P.; Friesen, R. W.; Girard, M.; Girard, Y.; Guay, J.; Riendeau, D.; Tagari, P.; Young, R. N. Bioorg. Med. Chem. Lett. 1998, 8, 1255; (f) Narender, P.; Srinivas, U.; Ravinder, M.; Rao, B. A.; Ramesh, C.; Harakishore, K.; Gangadasu, B.; Murthy, U. S. N.; Rao, V. J. Bioorg. Med. Chem. 2006, 14, 4600; (g) Muruganantham, N.; Sivakumar, R.; Anbalagan, N.; Gunasekaran, V.; Leonard, J. T. Biol. Pharm. Bull. 2004, 27, 1683; (h) Martirosyan, A. R.; Rahim-Bata, R.; Freeman, A. B.; Clarke, C. D.; Howard, R. L.; Strobl, J. S. Biochem. Pharmacol. 2004, 68, 1729; (i) Maguire, M. P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Zilberstein, A. J. Med. Chem. 1994, 37, 2129.
    5.(a) Aggarwal, A. K.; Jenekhe, S. A. Macromolecules 1991, 24, 6806; (b) Zhang, X.; Shetty, A. S.; Jenekhe, S. A. Macromolecules 1999, 32, 7422; (c) Jenekhe, S. A.; Lu, L.; Alam, M. M. Macromolecules 2001, 34, 7315.
    6.(a) Nalwa, H. S.; Suzuki, M.; Takahashi, A.; Kageyama, A. Appl. Phys. Lett. 1998, 72, 1311; (b) Concilio, S.; Pfister, P. M.; Tirelli, N.; Kocher, C.; Suter, U. W. Macromolecules 2001, 34, 3607.
    7.(a) Camps, R. Arch. Pharm. 1899, 237, 659; (b) Pflum, D. A. Camps Quinolinol Synthesis in Name Reactions in Heterocyclic Chemistry, Li, J. J.; Corey, E. J., Eds.; Wiley & Sons: Hoboken, NJ, 2005, 386; (c) Skraup, H. Ber. Dtsch. Chem. Ges. 1880, 13, 2086; (d) Friedlander, P. Chem. Ber. 1882, 15, 2572; (e) Friedländer, P.; Gohring, C. F.; Chem. Ber. 1883, 16, 1833; (f) Manske, R. H. F.; Kulka, M. Org. React. 1953, 7, 59; (g) Fehnel, E. A. J. Heterocycl. Chem. 1967, 4, 565; (h) Cheng, C.-C.; Yan, S.-J. Org. React. 1982, 28, 37; (i) Jones, G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol. 5, p 167; (j) Patil, N. T.; Raut, V, S. J. Org. Chem. 2010, 75, 6961; (k) Basavaiah, D.; Reddy, R. M.; Kumaragurubaran, N.; Sharada, D. S. Tetrahydron 2002, 58, 3693; (l) Shi, D.; Rong, L.; Wang, J.; Zhuang, Q.; Wang, X.; Tu, H.; Hu, H. J. Chem. Research (S), 2003, 342; (m) Cho, C. S.; Kim, J. S.; Oh, B. H.; Kim, T.-J.; Shim, S. C.; Yoon, N. S. Tetrahedron 2000, 56, 7747; (n) Cho, C. S.; Oh, B. H.; Shim, S. C. Tetrahedron Lett. 1999, 40, 1499; (o) Sangu, K.; Fuchibe, K.; Akiyama, T. Org. Lett. 2004, 6, 353; (p) Martinez, R.; Ramon, D. J.; Yus, M. J. Org. Chem. 2008, 73, 9778; (q) Sandelier, M. J.; Deshong, P. Org. Lett. 2007, 9, 3209; (r) Banwell, M. G.; Lupton, D. W.; Ma, X.; Renner, J.; Sydnes, M. O. Org. Lett. 2004, 6, 2741.
    8.Ramesh, C.; Kavala, V.; Kuo, C. W.; Raju, B. R.; Yao, C. F. Eur. J.Org. Chem. 2010. 3796.
    9.(a) List, B.; Pojarliev, P.; Martin. H. J. Org. Lett. 2001, 16, 2423; b) Saraswathi, V. G.; Sankararaman, S. J. Org. Chem. 1995, 60, 5024.
    Chapter-IV, Section A:
    IV.A.6. References:

    1.Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles, 2 nd, ed., Wiley-VCH, Weinheim, 2003.
    2.(a) La, D. S.; Belzile, J.; Bready, J. V.; Coxon, A.; DeMelfi, T.; Doerr, N.; Estrada, J.; Flynn, J. C.; Flynn, S. R.; Graceffa, R. F.; Harriman, S. P.; Larrow, J. F.; Long, A. M.; Martin, M. W.; Morrison, M. J.; Patel, V. F.; Roveto, P. M.; Wang, L.; Weiss, M. W.; Whittington, D. A.; Teffera, Y.; Zhao, Z. Y.; Polverino, A. J.; Harmang, J. C. J. Med. Chem. 2008, 51, 1695; (b) Has, J.; Tomasic, T.; Kikelj, D. J. Med. Chem. 2008, 51, 2863; (c) Has, J.; Jakopin, Z.; Bonrštnar, T.; Stegnar, M.; Kikelj, D. J. Med. Chem. 2008, 51, 5617.
    3. Frechette, R.; Weidner-Wells, M. A. WO Patent Appl. 9717333, 1997.
    4.Kikelj, D.; Suhadolc, E.; Rutar, A.; Pecar, S.; Puncuh, A.; Urleb, U.; Leskovsek, V.; Marc, G.; Sollner Dolenc, M.; Krbavcic, A.; Sersa, G.; Novakovic, S.; Povsic, L.; Stalc, A. European Patent EP0695308, 1996.
    5.Wise, L. D.; Wustrow, D. J.; Belliotti, T. WO Patent Appl. 9745419, 1997.
    6.(a) Chatterjee, A.; Basa, S. C. Chem. Ind. 1969, 11, 328; (b) Hofman, J.; Hofmanova, O. Eur. J. Biochem. 1969, 8, 109; (c) Otsuka, H.; Hirani, Y.; Nagao, T.; Yamasaki, K. J. Nat. Prod. 1988, 51, 74; (d) Tietze, L. F.; Beller, M.; Terfort, A.; Dolle, A. Synthesis 1991, 1118.
    7.Smid, P.; Coolen, H. K. A. C.; Keizer, H. G.; van Hes, R.; de Moes, J.-P.; den Hartog, A. P.; Stork, B.; Plekkenpol, R. H.; Niemann, L. C.; Stroomer, C. N. J.; Tulp, M. Th. M.; van Stuivenberg, H. H.; McCreary, A. C.; Hesselink, M. B.; Herremans, A. H. J.; Kruse, C. G. J. Med. Chem. 2005, 48, 6855.
    8.Fringuelli, R.; Pietrella, D.; Schiaffella, F.; Guarraci, A.; Perito, S.; Bistoni, F.; Vecchiarelli, A. Bioorg. Med. Chem. 2002, 10, 1681.
    9.Macchiarulo, A.; Costantino, G.; Fringuelli, D.; Vecchiarelli, A.; Schiaffella, F.; Fringuelli, R. Bioorg. Med. Chem. 2002, 10, 3415.
    10.Lanni, T. B., Jr.; Greene, K. L.; Kolz, C. N.; Para, K. S.; Visnick, M.; Mobley, J. L.; Dudley, D. T.; Baginski, T. J.; Liimatta, M. B. Bioorg. Med. Chem. Lett. 2007, 17, 756.
    11.Huang, M.-Z.; Huang, K.-L.; Ren, Y.-G.; Lei, M.-X.; Huang, L.; Hou, Z.-K.; Liu, A.-P.; Qu, X.-M. J. Agric. Food Chem. 2005, 53, 7908.
    12.Anderluh, M.; Cesar, J.; Stefanic, P.; Kikelj, D.; Janes, D.; Murn, J.; Nadrah, K.; Tominc, M.; Addicks, E.; Giannis, A.; Stegnar, M.; Dolenc, M. S. Eur. J. Med. Chem. 2005, 40, 25.
    13.Scheunemann, M.; Sorger, D.; Kouznetsova, E.; Sabri, O.; Schliebs, R.; Wenzel, B.; Steinbach, J. Tetrahedron Lett. 2007, 48, 5497.
    14.Niemeyer, H. M. Phytochemistry 1988, 27, 3349.
    15.Ilas, J.; Anderluh, P. S.; Dolenc, M. S.; Kikelj, D. Tetrahedron 2005, 61, 7325.
    16.(a) Feng, E.; Huang, H.; Zhou, Y.; Ye, D.; Jiang, H.; Liu, H. J. Org. Chem. 2009, 74, 2846; (b) Chen, D.; Shen, G.; Bao, W. Org. Biomol. Chem. 2009, 7, 4067.
    17.(a) Feng, G.; Wu, J.; Dai, W.-M. Tetrahedron Lett. 2007, 48, 401; (b) Yuan, Y.; Liu, G.; Li, L.; Wang, Z.; Wang, L. J. Comb. Chem. 2007, 9, 158; (c) Wu, J.; Nie, L.; Luo, J.; Dai, W.-M. Synlett 2007, 17, 2728; (d) Xing, X.; Wu, J.; Feng, G.; Dai, W.-M. Tetrahedron 2006, 62, 6774; (e) Feng, G.; Wu, J.; Dai, W.-M. Tetrahedron 2006, 62, 4635; (f) Dai, W.-M.; Wang, X.; Ma, C. Tetrahedron 2005, 61, 6879; (g) Rybczynski, P. J.; Zeck, R. E.; Combs, D. W.; Turchi, I.; Burris, T. P.; Xu, J. Z.; Yang, M.; Demarest, K. T. Bioorg. Med. Chem. Lett. 2003, 13, 235; (h) Matsumoto, Y.; Uchida, A.; Nakahara, H.; Yanagisawa, I.; Shibanuma, T.; Nohira, H. Chem. Pharm. Bull. 2000, 48, 428; (i) Hashimoto, Y.; Ishizaki, T.; Shudo, K. Tetrahedron 1991, 47, 1837; (j) Dudley, A. D.; Bunker, M. A.; Chi, L.; Cody, L. W.; Holland, R. D.; Ignasiak, P. D.; Dolphin, J.N.; McClanahan, B. T.; Mertz, E. T.; Narasimhan, S. L.; Rapundalo, T. S.; Trautschold, A. J.; Van Huis, A. C.; . Edmunds, J. J. J. Med. Chem. 2000, 43, 4063; (k) Sharifi, A.; Barazandeh, M.; Abaee, M. S.; Mizaei, M. Tetrahedron Lett. 2010, 51, 1852; (l) Brooks, G.; Dabbs, S.; Davies, D. T.; Hennessy, A. J.; Jones, G. E.; Markwell, R. E.; Miles, T. J.; Owston, N. A.; Pearson, N. D.; Peng, T. W. Tetrahedron Lett. 2010, 51, 5035; (m) Borate, H. B.; Maujan, S. R.; Sawargave, S. P.; Chandavarkar, M. A.; Vaiude, S. R.; Joshi, V. A.; Wakharkar, R. D.; Iyer, R.; Kelkar, R. G.; Chanvan, S. P.; Kunte, S. S. Bioorg. Med. Chem. Lett. 2010, 20, 722.
    18.(a) Kundu, N. G.; Chaudhuri, G.; Upadhyay, A. J. Org. Chem. 2001, 66, 20; (b) Henry, N.; Guillaumet, G.; Pujol, M. D. Tetrahedron Lett. 2004, 45, 1465.
    19.Atkinson, J.; Morand, P.; Arnason, T. J. Org. Chem. 1991, 56, 1788.
    20.Ma, Y.; Zhang, Y. J. Chem. Res. 2000, 388.
    21.Ozden, S.; Ozturk, A. M.; Goker, H.; Altanlar, N. Il Farmaco. 2000, 55, 715.
    22.(a) Breznik, M.; Mrcina, A.; Kikelj, D. Tetrahedron: Asymmetry 1998, 9, 1115; (b) Stefanic, P.; Turnsek, K.; Kikelj, D. Tetrahedron 2003, 59, 7123.
    23. Zuo, H.; Meng. L.; Ghate. M.; Hwang. K. H.; Cho.Y. K.; Chandrasekhar, S.; Raji Reddy. Ch.; Shin. D. S. Tetrahedron Lett. 2008, 49, 3827.
    24.Lee, C. L.; Chan, K. P.; Larn, Y.; Lee, S. Y. Tetrahedron Lett. 2001, 42, 1167.
    25.(a) Ramesh, C.; Kavala, V.; Raju, B. R.; Kuo, C. W.; Yao, C.-F. Tetrahedron Lett. 2009, 50, 4037; (b) Ramesh, C.; Kavala, V.; Kuo, C. W.; Raju, B. R.; Yao, C.-F. Eur. J.Org. Chem. 2010, 3796; (c) Ramesh, C.; Kavala, V.; Kuo, C. W.; Yao, C.-F. Tetrahedron Lett. 2010, 51, 5234.
    26. Rao, K. V. P.; Reddy, P. S. N.; Sundaramurthy,V. Indian J. Chem., Sect. B 1985 , 24, 1120.
    Chapter-IV, Section B:
    IV.B.6. References
    1.(a) Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn, M. R.; Emmert, D. E.;Garmon, S. A.; Graber, D. R.; Grega, K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer, R. J.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H. J. Med. Chem. 2000, 43, 953; (b) Buckle, D. R.; Rockell, C. J. M.; Smith, H.; Spicer, B. A. J. Med. Chem. 1986, 29, 2262; (c) Joan, C. F. T.; Elizabeth, H.; Beatrice, M.; Daniel, P. B. Antimicrob. Agents Chemother. 1998, 42, 313; (d) Vicentini, C. B.; Brandolini, V.; Guarneri, M.; Giori, P. Farmaco 1992, 47, 1021; (e) Palhagen, S.; Canger, R.; Henriksen, O.; van Parys, J. A.; Riviere, M.-E.; Karolchyk, M. A. Epilepsy Res. 2001, 43, 115; (f) Alvarez, R.; Velazquez, S.; San, F.; Aquaro, S.; De, C.; Perno, C. F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. J. Med. Chem. 1994, 37, 4185.
    2.Gouault, N.; Cupif, J. F.; Sauleau, A.; David, M. Tetrahedron Lett. 2000, 41, 7293.
    3.(a) Mamidyala, S. K.; Finn, M. G. Chem. Soc. Rev. 2010, 39, 1252; (b) Jewett, J. C.; Bertozzi, C. R. Chem. Soc. Rev. 2010, 39, 1272; (c) Hua, Y.; Flood, A. H. Chem. Soc. Rev. 2010, 39, 1262; (d) Kappe, C. O.; Eycken, E. V.; Chem. Soc. Rev. 2010, 39, 1280; (e) Buckley, B. R.; Dann, S. E.; Heaney, H. Chem. Eur. J. 2010, 6278; (f) Spiteri, C.; Moses, J. E. Angew. Chem. Int. Ed. 2010, 49, 31.
    4.(a) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057; (b) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596.
    5.(a) Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952; (b) Rongti, L.; Jansen, D. J.; Datta, A. Org. Biomol. Chem. 2009, 7, 1921.
    6.(a) Chandrasekhar, S.; Seenaiah, M.; Kumar, A.; Reddy, C. R.; Mamidyala, S. K.; Kumar, C. G.; Balasubramanian, S. Tetrahedron Lett. 2011, 52, 806; (b) Chowdhury, C.; Mandal, S. B.; Achari, B. Tetrahedron Lett. 2005, 46, 8531; (c) Chowdhury, C.; Mukherjee, S.; Das, B.; Achari, B. J. Org. Chem. 2009, 74, 3612; (d) Chowdhury, C.; Sasmal, A. K.; Dutta, P. K. Tetrahedron Lett. 2009, 50, 2678; (e) Nandivada, H.; Ziang, X.; Lahann, J. J. Adv. Mater. 2007, 19, 2197; (f) Buckle, D. R.; Rockell, C. J. M.; Smith, H.; Picer, B. A. J. Med. Chem. 1986, 29, 2262; (g) Roper, S.; Franz, M. H.; Wart chow, R.; Hoffmann, H. M. R. Org. Lett. 2003, 5, 2773; (h) Panteleev, J.; Geyer, K.; Aguilar, A. A.; Wang, L.; Lautens, M. Org. Lett. 2010, 12, 5092; (i) Oliva, A.I.; Christmann, U.; Font, D.; Cuevas, F.; Ballester, P.; Buschmann, H.; Torrens, A.; Yenes, S.; Pericas, M. A. Org. Lett. 2008, 10, 1617; (j) Sudhir, V. S.; Kumar, N. Y. P.; Baig, R. B. N.; Chandrasekaran, S. J. Org. Chem. 2009, 74, 7588; (k) Brawn, R. A.; Welzel, M.; Lowe, J. T.; Panek, J. S. Org. Lett. 2010, 12, 336; (l) Balducci, E.; Bellucci, L.; Petricci, E.; Taddei, M.; Tafi, A. J. Org. Chem. 2009, 74, 1314; (m) Angell, Y.; Burgess, K. J. Org. Chem. 2005, 70, 9595.
    7.(a) Kumar, D.; Reddy, V. B.; Varma, R. S. Tetrahedran Lett. 2009, 50, 2065; (b) Kamal, A.; Shankaraiah, N.; Devaiah, V.; Reddy, K. L.; Juvekar, A.; Sen, S.; Kurian, N.; Zingde, S. Bioorg. Med. Chem. Lett. 2008, 18, 1468; (c) Alvarez, R.; Valazquez, S.; San, F.; De, S.; Aquaroperno, C. C. F.; Karlsson, A.; Balzarini, J.; Camarassa, M. J. J. Med. Chem. 1994, 37, 4185; (d) Feldman, A. K.; Colasson, B.; Fokin, V. V. Org. Lett. 2004, 6, 3897; (e) Velazquez, S.; Alvarez, R.; Perez, C.; Cago, F.; De, C.; Camarassa, M. J. B. Antivir. Chem. Chemother. 1998, 9, 481; (f) Yan, W.; Wang, Q.; Chen, J.; Petersen, J. L.; Shi, X. Org. Lett. 2010, 12, 3308; (g) Sreedhar, B.; Reddy, P. S.; Krishna, V. R. Tetrahedran Lett. 2007, 48, 5831; (h) Shi, F.; Waldo, J. P.; Chen, Y.; Larock, R. C. Org. Lett. 2008, 10, 2409; (i) Juwarker, H.; Lenhardt, J. M.; Castillo, J.; Zhao, E.; Krishnamurthy, S.; Jamiolkowski, R. M.; Kim, K. H.; Craig, S. L. J. Org. Chem. 2009, 74, 8924.
    8.(a) Bodine, K. D.; Gin, D. Y.; Gin, M. S. J. Am. Chem. Soc. 2004, 126, 1638; (b) Bogdan, A. R.; James, K. Chem. Eur. J. 2010, 14506; (b) Dorner, S.; Westermann, B. Chem. Commun. 2005, 2852; (c) Marcaurelle, L. A.; Comer, E.; Dandapani, S.; Duvall, J. R.; Gerard, B.; Kesavan, S.; Lee IV, M. D.; Liu, H.; Lowe, J. T.; Marie, J. C.; Mulrooney, C. A.; Pandya, B. A.; Rowley, A.; Ryba, T.D.; Suh, B. C.; Wei, J.; Young, D. W.; Akella, L. B.; Ross, N. T.; Zhang, Y. L.; Fass, D. M.; Reis, S. A.; Zhao, W. N.; Haggarty, S. J.; Palmer, M.; Foley, M. A. J. Am. Chem. Soc. 2010, 132, 16962; (d) Billing, J. F.; Nilsson, U. J. J. Org. Chem. 2005, 70, 4847; (e) Punna, S.; Kuzelka, J.; Wang, Q.; Finn, M. G. Angew. Chem. Int. Ed. 2005, 44, 2215; (f) Dorner, S.; westermann. B. Chem. Commun. 2005, 2852.
    9.(a) van Maarseveen, J. H.; Horne, W. S.; Ghadiri, M. R. Org. Lett. 2005, 7, 4503; (b) Bock, V. D.; Perciaccante, R.; Jansen, T. P.; Hiemstra, H.; Maarseveen, J. H. V. Org. Lett. 2006, 8, 919; (c) Oh, K.; Guan, Z. Chem. Commun. 2006, 3069; (d) Ahsanullah, Schmieder, P.; Kuhne, R.; Rademann, J. Angew. Chem. Int. Ed. 2009, 48, 5042; (e) Bonnet, D.; Riche, S.; Loison, S.; Dagher, R.; Frantz, M. C.; Boudier, L.; Rahmeh, R.; Mouillac, B.; Haiech, J.; Hibert, M. Chem. Eur. J. 2008, 6247; (f) Tam, A.; Arnold, U.; Soellner, M. B.; Raines, R. T. J. Am. Chem. Soc. 2007, 129, 12670; (g) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134; (i) Whiting, M.; Muldoon, J.; Lin, Y. C.; Silverman, S. M.; Lindstrom, W.; Olson, A. J.; Kolb, H. C.; Finn, M. G.; Sharpless, K. B.; Elder, J. H.; Fokin, V. V. Angew. Chem. Int. Ed. 2006, 45, 1435.
    10.(a) Al-Maoudi, N. A.; Al-Soud, A. Y. Tetrahedron Lett. 2002, 43, 4021; (b) Chandrasekhar, S.; Rao, C. L.; Nagesh, C.; Reddy, C. R.; Sridhar, B. Tetrahedron Lett. 2007, 48, 5869; (c) Kuijpers, B. H. M.; Groothuys, S.; Keereweer, A. B. R.; Quaedflieg, P. J. L. M.; Blaauw, R. H.; van Delft, F. L.; Rutjes, F. P. J. T. Org. Lett. 2004, 6, 3123; (d) Dondoni, A.; Giovannini, P. P.; Massi, A. Org. Lett. 2004, 6, 2929; (e) Srinivas, Ch.; Fang, X.; Wang, Q. Tetrahedron Lett. 2005, 46, 2331; (f) Aizpurua, J. M.; Azcune, I.; Fratila, R. M.; Balentova, E.; Aizpurua, M. S.; Miranda, J. I. Org. Lett. 2010, 12, 1584; (g) Hotha, S.; Anegundi, R. I.; Natu, A. A. Tetrahedron Lett. 2005, 46, 4585; (h) Cecioni, S.; Faure, S.; Darbost, U.; Bonnamour, I.; Lopez, H. P.; Roy, O.; Taillefumier, C.; Wimmerova, M.; Praly, J. P.; Imberty, A.; Vidal, S. Chem. Eur. J. 2011, 2146; (i) Hotha, S.; Kashyap, S. J. Org. Chem. 2006, 71, 364.
    11.(a) Macchiarulo, A.; Costantino, G.; Fringuelli, D.; Vecchiarelli, A.; Schiaffella, F.; Fringuelli, R. Bioorg. Med. Chem. 2002, 10, 3415; (b) Smid, P.; Coolen, H. K. A. C.; Keizer, H. G.; van Hes, R.; de Moes, J.-P.; den Hartog, A. P.; Stork, B.; Plekkenpol, R. H.; Niemann, L. C.; Stroomer, C. N. J.; Tulp, M. Th. M.; van Stuivenberg, H. H.; McCreary, A. C.; Hesselink, M. B.; Herremans, A. H. J.; Kruse, C. G. J. Med. Chem. 2005, 48, 6855; (c) Lanni, T. B., Jr.; Greene, K. L.; Kolz, C. N.; Para, K. S.; Visnick, M.; Mobley, J. L.; Dudley, D. T.; Baginski, T. J.; Liimatta, M. B. Bioorg. Med. Chem. Lett. 2007, 17, 756; (d) Fringuelli, R.; Pietrella, D.; Schiaffella, F.; Guarraci, A.; Perito, S.; Bistoni, F.; Vecchiarelli, A. Bioorg. Med. Chem. 2002, 10, 1681; (e) Anderluh, M.; Cesar, J.; Stefanic, P.; Kikelj, D.; Janes, D.; Murn, J.; Nadrah, K.; Tominc, M.; Addicks, E.; Giannis, A.; Stegnar, M.; Dolenc, M. S. Eur. J. Med. Chem. 2005, 40, 25; (f) Scheunemann, M.; Sorger, D.; Kouznetsova, E.; Sabri, O.; Schliebs, R.; Wenzel, B.; Steinbach, J. Tetrahedron Lett. 2007, 48, 5497; (g) Niemeyer, H. M. Phytochemistry 1988, 27, 3349.
    12.(a) Borate, B.; H, Maujan, R.; S, Sawargave, P.; S, Chandavarkar, A.; M, Vaiude, R.; S, Joshi, A.; V, Wakharkar, D.; R, Iyer, R, Kelkar, G.; R, Chavan, P.; S, Kunte, S.; S. Bioorg. Med. Chem. Lett. 2010, 20, 722; (b) Li, A.-R.; Zhang, J.; Greenberg, J.; Lee, T. W.; Liu, J. Bioorg. Med. Chem. Lett. 2011, 21, 2472; (c) Schiaffella, F, Macchiarulo, A, Milanese, L, Vecchiarelli, A, Costantino, G, Pietrella, D, Fringuelli, R. J. Med. Chem. 2005, 48, 7658; (d) Fringuelli, R.; Pietrella, D.; Schiaffella, F.; Guarraci, A.; Perito, S.; Bistoni, F.; Vecchiarelli, A. Bioorg. Med. Chem. 2002, 10, 1681; (e) Macchiarulo, A, Costantino, G, Fringuelli, D, Vecchiarelli, A, Schiaffella, F, Fringuelli, R. Bioorg. Med. Chem. 2002, 10, 3415; (f) Fringuelli, R, Giacche, N, Milanese, L, Cenci, E, Macchiarulo, A, Vecchiarelli, A, Costantino, G, Schiaffella, F. Bioorg. Med. Chem. 2009, 17, 3838.
    13.Ramesh, C.; Raju, B. R.; Kavala, V.; Kuo, C. W.; Yao, C.-F. Tetrahedron 2011, 67, 1187.
    14.(a) Rao, K. V. P.; Reddy, P. S. N.; Sundaramurthy, V. Indian J. Chem., Sect. B 1985, 24, 1120; (b) Verduyn, L. S. C.; Mirfeizi, L.; Dierckx, R. A.; Elsinga, P. H.; Fering, B. L. Chem. Commun. 2009, 2139; (c) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413; (d) López, P. R.; Torre, M. C. D. L.; Montenegro, H. E.; Asenjo, M.; Sierra, M. A. Org. Lett. 2008, 10, 3555.

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