Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2013; 24(12): 1549-1554
DOI: 10.1055/s-0033-1339193
DOI: 10.1055/s-0033-1339193
letter
Synthesis of 2-Aryl Benzothiazoles via K2S2O8-Mediated Oxidative Condensation of Benzothiazoles with Benzylamines
Further Information
Publication History
Received: 17 April 2013
Accepted after revision: 18 May 2013
Publication Date:
17 June 2013 (online)
Abstract
A novel way to synthesize 2-arylbenzothiazoles is described. Reactions of benzothiazoles with diverse benzylamines in the presence of K2S2O8 and KOt-Bu in DMSO–H2O afforded the desired 2-arylbenzothiazoles in good yields. It is notable that no transition-metal catalyst is needed in this reaction. Compared with other known methods, this method of synthesizing 2-arylbenzothiazoles can be advantageous in cases where substituted benzothiazoles and benzylamines are readily available.
Supporting Information
- Experimental procedures, characterization data, and copies of 1H NMR and 13C NMR spectra for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
- 1a Dondoni A. Comprehensive Heterocyclic Chemistry II . Vol. 3. Shinkai IE. Pergamon Press; Glasgow: 1996: 373
- 1b Chen CP, Chen YJ. Tetrahedron Lett. 2004; 45: 113
- 1c Hutchinson I, Stevens MF. G, Westwell AD. Tetrahedron Lett. 2000; 41: 425
- 1d Das J, Chen P, Norris D, Padmanabha R, Lin J, Moquin RV, Shen Z, Cook LS, Doweyko AM, Pitt S, Pang S, Shen DR, Fang Q, de Fex HF, McIntyre KW, Shuster DJ, Gillooly KM, Behnia K, Schieven GL, Wityak J, Barrish JC. J. Med. Chem. 2006; 49: 6819
- 1e Borzilleri RM, Bhide RS, Barrish JC, D’Arienzo CJ, Derbin GM, Fargnoli J, Hunt JT, Jeyaseelan R, Kamath A, Kukral DW, Marathe P, Mortillo S, Qian L, Tokarski JS, Wautlet BS, Zheng X, Lombardo LJ. J. Med. Chem. 2006; 49: 3766
- 2a Schwander H In Ullman’s Encyclopedia of Industrial Chemistry . Vol. A11. VCH; Weinheim: 1988: 279
- 2b Mori A, Sekiguchi A, Masui K, Shimada T, Horie M, Osakada K, Kawamoto M, Ikeda T. J. Am. Chem. Soc. 2003; 125: 1700
- 2c Lion CJ, Matthews CS, Wells G, Bradshaw TD, Stevens MF. G, Westwell AD. Bioorg. Med. Chem. Lett. 2006; 16: 5005
- 2d Huang ST, Hsei IJ, Chen C. Bioorg. Med. Chem. 2006; 14: 6106
- 2e Giltaire S, Herphelin F, Frankart A, Herin M, Stoppie P, Poumay Y. Brit. J. Dermatol. 2009; 160: 505
- 3a Itoh T, Nagata K, Ishikawa H, Ohsawa A. Heterocycles 2004; 63: 2769
- 3b Bahrami K, Khodaei MM, Naali F. J. Org. Chem. 2008; 73: 6835
- 3c Parikh N, Kumar D, Roy SR, Chakraborti AK. Chem. Commun. 2011; 47: 1797
- 3d Riadi Y, Mamouni R, Azzalou R, Haddad ME, Routier S, Guillaumet G, Lazar S. Tetrahedron Lett. 2011; 52: 3492
- 4a Rudrawar S, Kondaskar A, Chakraborti AK. Synthesis 2005; 2521
- 4b Sharghi H, Asemani O. Synth. Commun. 2009; 39: 860
- 5 Hein DW, Alheim RJ, Leavitt JJ. J. Am. Chem. Soc. 1957; 79: 427
- 6 Nadaf RN, Siddiqui SA, Thomas D, Lahoti RJ, Srinivasan KV. J. Mol. Catal. A: Chem. 2004; 214: 155
- 7a Wilfred CD, Taylor RJ. K. Synlett 2004; 1628
- 7b Raghavendra GM, Ramesha AB, Revanna CN, Nandeesh KN, Mantelingu K, Rangappa KS. Tetrahedron Lett. 2011; 52: 5571
- 8 Liao Y, Qi H, Chen S, Jiang P, Zhou W, Deng G.-J. Org. Lett. 2012; 14: 6004
- 9 Nguyen TB, Ermolenko L, Dean WA, Al-Mourabit A. Org. Lett. 2012; 14: 5948
- 10a Kondo Y, Komine T, Sakamoto T. Org. Lett. 2000; 2: 3111
- 10b Sezen B, Sames D. Org. Lett. 2003; 5: 3607
- 10c Chiong H, Daugulis O. Org. Lett. 2007; 9: 1449
- 10d Turner GL, Morris JA, Greaney MF. Angew. Chem. Int. Ed. 2007; 46: 7996
- 10e Do HQ, Daugulis O. J. Am. Chem. Soc. 2007; 129: 12404
- 10f Lewis J, Berman A, Bergman R, Ellman J. J. Am. Chem. Soc. 2008; 130: 2493
- 10g Canivet J, Yamaguchi J, Ban I, Itami K. Org. Lett. 2009; 11: 1733
- 10h Zhao D, Wang W, Yang F, Lan J, Yang L, Gao G, You J. Angew. Chem. Int. Ed. 2009; 48: 3296
- 10i Huang J, Chan J, Chen Y, Borths CJ, Baucom KD, Larsen RD, Faul MM. J. Am. Chem. Soc. 2010; 132: 3674
- 10j Shibahara F, Yamaguchi E, Murai T. Chem. Commun. 2010; 46: 2471
- 10k Shibahara F, Yamaguchi E, Murai T. J. Org. Chem. 2011; 76: 2680
- 10l Yamamoto T, Muto K, Komiyama M, Canivet J, Yamaguchi J, Itami K. Chem. Eur. J. 2011; 36: 10113
- 11a Zhang F, Greaney MF. Angew. Chem. Int. Ed. 2010; 49: 2768
- 11b Xie K, Yang Z, Zhou X, Li X, Wang S, Tan Z, An X, Guo C.-C. Org. Lett. 2010; 12: 1564
- 12a Guchhait SK, Kashyap M, Saraf S. Synthesis 2010; 1166
- 12b Ranjit S, Liu X. Chem. Eur. J. 2011; 17: 1105
- 12c Kirchberg S, Tani S, Ueda K, Yamaguchi J, Studer A, Itami K. Angew. Chem. Int. Ed. 2011; 50: 2387
- 13a Yokooji A, Okazawa T, Satoh T, Miura M, Nomura M. Tetrahedron 2003; 59: 5685
- 13b Hachiya H, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2010; 49: 2202
- 13c Organ MG, Abdel-Hadi M, Avola S, Hadei N, Nasielski J, O’Brien CJ, Valente C. Chem. Eur. J. 2007; 13: 150
- 14a Bose DS, Idrees M. J. Org. Chem. 2006; 71: 8261
- 14b Itoh T, Mase T. Org. Lett. 2007; 9: 3687
- 14c Ueda S, Nagasawa H. Angew. Chem. Int. Ed. 2008; 47: 6411
- 14d Ma D, Xie S, Xue P, Zhang X, Dong J, Jiang Y. Angew. Chem. Int. Ed. 2009; 48: 4222
- 15a Liu S, Chen R, Guo X, Yang H, Deng G, Li C.-J. Green Chem. 2012; 14: 1577
- 15b Yang Z, Chen X, Wang S, Liu J, Xie K, Tan Z. J. Org. Chem. 2012; 77: 7086
- 16 For the synthesis of 2-benzoyl benzothiazole from benzothiazole and acetophenone via thiazole ring-opening–recyclization strategy, see: Gao Q, Wu X, Jia F, Liu M, Zhu Y, Cai Q, Wu A. J. Org. Chem. 2013; 78: 2792
- 17 Bahman T, Hamid Y. Tetrahedron 1997; 53: 7889
- 18 Su F, Mathew SC, Möhimann L, Antonietti M, Wang X, Blechert S. Angew. Chem. Int. Ed. 2011; 50: 657