Synthesis, Inhaltsverzeichnis Synthesis 2012; 44(16): 2579-2586DOI: 10.1055/s-0032-1316670 paper © Georg Thieme Verlag Stuttgart · New York Thermally Induced Cyclization of Electron-Rich N-Arylthiobenzamides to Benzothiazoles Oscene V. Barrett Department of Chemistry, University of the West Indies, Mona, Kingston 7, Jamaica , Fax: +1876(977)1835 eMail: yvette.jackson@uwimona.edu.jm , Nadale K. Downer-Riley Department of Chemistry, University of the West Indies, Mona, Kingston 7, Jamaica , Fax: +1876(977)1835 eMail: yvette.jackson@uwimona.edu.jm , Yvette A. Jackson* Department of Chemistry, University of the West Indies, Mona, Kingston 7, Jamaica , Fax: +1876(977)1835 eMail: yvette.jackson@uwimona.edu.jm › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract Heating N-(2-methoxyphenyl)benzenecarbothioamides in refluxing nitrobenzene for 24 hours gives the corresponding benzothiazoles with intramolecular ipso substitution of the ortho-methoxy substituent. The thermal cyclization of various other N-arylthiobenzamides is also explored. Key words Key wordscyclizations - heterocycles - thioamides Volltext Referenzen References 1a Hari N, Tsukamoto G, Imamura A, Ohashi M, Saito T, Yoshino K. Chem. Pharm. Bull. 1992; 40: 2390 1b Henriksen G, Hauser AI, Westwell AD, Yousefi BH, Schwaiger M, Drzezga A, Wester H.-J. J. Med. Chem. 2007; 50: 1087 1c Kok SH. L, Gambari R, Chui CH, Yuen MC. W, Lin E, Wong RS. M, Lau FY, Cheng GY. M, Lam WS, Chan SH, Lam KH, Cheng CH, Lai PB. S, Yu MW. Y, Cheung F, Tang JC. O, Chan AS. C. Bioorg. Med. Chem. 2008; 16: 3626 1d Liu C, Lin J, Pitt S, Zhang RF, Sack JS, Kiefer SE, Kish K, Doweyko AM, Zhang H, Marathe PH, Trzaskos J, Mckinnon M, Dodd JH, Barrish JC, Schieven GL, Leftheris K. Bioorg. Med. Chem. Lett. 2008; 18: 1874 1e Serdons K, Verduyckt T, Vanderghinste D, Borghgraef P, Cleynhens J, Van Leuven F, Kung H, Bormans G, Verbruggen A. Eur. J. Med. Chem. 2009; 44: 1415 For selected reviews on the synthesis of benzothiazole ring systems, see: 2a Yadav PS, Devprakash Senthilkumar GP. Int. J. Pharm. Sci. Drug Res. 2011; 3: 1 2b Weekes AA, Westwell AD. Curr. Med. Chem. 2009; 16: 2430 2c Gupta A, Rawat S. J. Curr. Pharm. Res. 2010; 3: 13 3 Downer NK, Jackson YA. Org. Biomol. Chem. 2004; 2: 3039 4 Barrett OV, Downer-Riley NK, Jackson YA. Heterocycles 2010; 81: 1641 5 Jackson YA, Lyon MA, Townsend N, Bellabe K, Soltanik F. J. Chem. Soc., Perkin Trans. 1 2000; 205 6 Lyon MA, Lawrence S, Williams DJ, Jackson YA. J. Chem. Soc., Perkin Trans. 1 1999; 437 7 Bunnett JF, Hrutfiord BF. J. Am. Chem. Soc. 1961; 83: 1691 8a Fields EK, Meyerson S. J. Org. Chem. 1972; 37: 3861 8b Chon J, Paik W. Bull. Korean Chem. Soc. 1983; 4: 55 9 Buchwald SL, Bolm C. Angew. Chem. Int. Ed. 2009; 48: 5586 10 Larsson P.-F, Correa A, Carril M, Norrby P.-O, Bolm C. Angew. Chem. Int. Ed. 2009; 48: 5691 11 Taillefer M, Xia N, Ouali A. Angew. Chem. Int. Ed. 2007; 46: 934 12 Bowman WR, Heaney H, Jordan BM. Tetrahedron 1991; 47: 10119 13 Evindar G, Batey R. J. Org. Chem. 2006; 71: 1802 14 Toyofuku SK, Iwasaki UA. US 5,446,010, 1995 15 Babu S, Vommina V. Tetrahedron Lett. 2005; 46: 4099 16 Ueda S. J. Org. Chem. 2009; 74: 4272 17 Wolfe JF, Loo BH, Arnold FE. Macromolecules 1981; 14: 915 18 Stevens MF. G, McCall CJ, Lelievald P, Alexander P, Richter A, Davies DE. J. Med. Chem. 1994; 37: 1689 19 Petrova D, Kostos V, Petrov I. J. Mol. Struct. 1986; 142: 459 20 Swenton JS, Bonke BR, Clark WM, Chen CP, Martin KV. J. Org. Chem. 1990; 55: 2027 21 Finzi C, Grabdolini G. Gazz. Chim. Ital. 1959; 89: 2543
