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Synthesis 2013; 45(7): 943-951
DOI: 10.1055/s-0032-1318304
DOI: 10.1055/s-0032-1318304
paper
Synthesis of 2-Substituted Benzothiazoles from 1-Iodo-2-nitrobenzenes by a Copper-Catalyzed One-Pot Three-Component Reaction
Weitere Informationen
Publikationsverlauf
Received: 15. Dezember 2012
Accepted after revision: 31. Januar 2013
Publikationsdatum:
27. Februar 2013 (online)
Abstract
A novel method was developed for synthesizing 2-substituted 1,3-benzothiazoles through a copper-catalyzed, one-pot, three-component reaction of a 1-iodo-2-nitrobenzene with sodium sulfide and an aldehyde.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are experimental procedures and 1H NMR and 13C NMR spectra data for all the products.
- Supporting Information
-
References
- 1a Mortimer CG, Wells G, Crochard J.-P, Stone EL, Bradshaw TD, Stevens MF. G, Westwell AD. J. Med. Chem. 2006; 49: 179
- 1b Chakraborty M, Jin KJ, Brewer SC, Peng H.-L, Platz MS, Novak M. Org. Lett. 2009; 11: 4862
- 2 Palmer PJ, Trigg RB, Warrington JV. J. Med. Chem. 1971; 14: 248
- 3 Gupta A, Rawat S. J. Chem. Pharm. Res. 2010; 2: 244
- 4 Neres J, Brewer ML, Ratier L, Botti H, Buschiazzo A, Edwards PN, Mortenson PN, Charlton MH, Alzari PM, Frasch AC, Bryce RA, Douglas KT. Bioorg. Med. Chem. Lett. 2009; 19: 589
- 5 Sun Q, Wu R, Cai S, Lin Y, Sellers L, Sakamoto K, He B, Peterson BR. J. Med. Chem. 2011; 54: 1126
- 6 Black C, Deschenes D, Gagnon M, Lachance N, Leblanc Y, Leger S, Li CS, Oballa RM. WO 2007009236, 2007
- 7 Han J, Burgess K. Chem. Rev. 2010; 110: 2709
- 8a Boger DL. J. Org. Chem. 1978; 43: 2296
- 8b Terashima M, Ishii M, Kanaoka Y. Synthesis 1982; 484
- 8c Couture A, Grandclaudon P. Heterocycles 1984; 22: 1383
- 8d Bougrin K, Loupy A, Soufiaoui M. Tetrahedron 1998; 54: 8055
- 8e Mourtas S, Gatos D, Barlos K. Tetrahedron Lett. 2001; 42: 2201
- 8f Matsushita H, Lee S.-H, Joung M, Clapham B, Janda KD. Tetrahedron Lett. 2004; 45: 313
- 8g Rudrawar S, Kondaskar A, Chakraborti AK. Synthesis 2005; 2521
- 8h Rodionov VO, Presolski SI, Gardinier S, Lim Y.-H, Finn MG. J. Am. Chem. Soc. 2007; 129: 12696
- 8i Bahrami K, Khodaei MM, Naali F. J. Org. Chem. 2008; 73: 6835
- 8j Parikh N, Kumar D, Raha Roy S, Chakraborti AK. Chem. Commun. (Cambridge) 2011; 47: 1797
- 9a Benedí C, Bravo F, Uriz P, Fernández E, Claver C, Castillón S. Tetrahedron Lett. 2003; 44: 6073
- 9b Evindar G, Batey RA. J. Org. Chem. 2006; 71: 1802
- 9c Vera MD, Pelletier JC. J. Comb. Chem. 2007; 9: 569
- 9d Bernardi D, Ba LA, Kirsch G. Synlett 2007; 2121
- 9e Saha P, Ramana T, Purkait N, Ali MA, Paul R, Punniyamurthy T. J. Org. Chem. 2009; 74: 8719
- 9f Jaseer EA, Prasad DJ. C, Dandapat A, Sekar G. Tetrahedron Lett. 2010; 51: 5009
- 10a Ma D, Xie S, Xue P, Zhang X, Dong J, Jiang Y. Angew. Chem. Int. Ed. 2009; 48: 4222
- 10b Itoh T, Mase T. Org. Lett. 2007; 9: 3687
- 11a Deng H, Li Z, Ke F, Zhou X. Chem. Eur. J. 2012; 18: 4840
- 11b Park N, Heo Y, Kumar MR, Kim Y, Song KH, Lee S. Eur. J. Org. Chem. 2012; 1984
- 12 Only two cases have been reported in which benzothiazoles were obtained in low yields in a single step from 1-iodo-2-nitrobenzenes and thiobenzyl alcohols, see: Duan Z, Ranjit S, Liu X. Org. Lett. 2010; 12: 2430
- 13 Ono N. The Nitro Group in Organic Synthesis . Wiley-VCH; New York: 2001
- 14a Li YG, Xu YF, Qian XH, Qu BY. Tetrahedron Lett. 2004; 45: 1247
- 14b Li ZG, Yang Q, Qian XH. Bioorg. Med. Chem. 2005; 13: 3149
- 14c Li ZG, Yang Q, Qian XH. Tetrahedron 2005; 61: 6634
- 15a Šrogl J, Hývl J, Révész Á, Schröder D. Chem. Commun. (Cambridge) 2009; 3463
- 15b Hývl J, Šrogl J. Eur. J. Org. Chem. 2010; 2849
- 15c Rokob TA, Rulíšek L, Šrogl J, Révész Á, Zins EL, Schröder D. Inorg. Chem. 2011; 50: 9968
- 16 Canivet J, Yamaguchi J, Ban I, Itami K. Org. Lett. 2009; 11: 1733
- 17 Ha YM, Park JY, Park YJ, Park D, Choi YJ, Kim JM, Lee EK, Han YK, Kim J.-A, Lee JY, Moon HR, Chung HY. Bioorg. Med. Chem. Lett. 2011; 21: 2445
- 18 Choi SJ, Park HJ, Lee SK, Kim SW, Han G, Choo HY. P. Bioorg. Med. Chem. 2006; 14: 1229
- 19 Hashem S, Omid A. Synth. Commun. 2009; 39: 860
- 20 Itoh T, Nagata K, Ishikawa H, Ohsawa A. Heterocycles 2004; 63: 2769
- 21 Huang JK, Chan J, Chen Y, Borths CJ, Baucom KD, Larsen RD, Faul MM. J. Am. Chem. Soc. 2010; 132: 3674
- 22 Bandyopadhyaya P, Sathea M, Prasada GK, Sharmab P, Kaushik MP. J. Mol. Catal. A: Chem. 2011; 341: 77
- 23 Fan XS, He Y, Zhang XY, Guo SH, Wang YY. Tetrahedron 2011; 67: 6369
- 24 Inamoto K, Hasegawa C, Hiroya K, Doi T. Org. Lett. 2008; 10: 5147
- 25 Stevens MF. G, McCall CJ, Lelieveld P, Alexander P, Richter A, Davies DE. J. Med. Chem. 1994; 37: 1689
- 26 Yoshino K, Kohno T, Uno T, Morita T, Tsukamoto G. J. Med. Chem. 1986; 29: 820
- 27 Roe A, Tucker WP. J. Heterocycl. Chem. 1965; 2: 148
- 28 Kohichiro Y, Noriyuki H, Manabu H, Tominori M, Goro T. J. Heterocycl. Chem. 1989; 26: 1039
- 29 Alagille D, Baldwina RM, Tamagnan GD. Tetrahedron Lett. 2005; 46: 1349
- 30 Bose DS, Idrees M. J. Org. Chem. 2006; 71: 8261
- 31 Matloubi Moghaddam F, Zali Boeini H. Synlett 2005; 1612
- 32 Osuka A, Uno Y, Horiuchi H, Suzuki H. Synthesis 1984; 145
- 33 Nagase R, Kawashima T, Yoshifuji M, Inamoto N. Heterocycles 1977; 8: 243