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-00000084.xml
Synthesis 2013; 45(2): 219-224
DOI: 10.1055/s-0032-1317930
DOI: 10.1055/s-0032-1317930
paper
A Rapid and Convenient Microwave-Promoted Synthesis of 3,5-Disubstituted 2-Chloropyridines and Their Conversion into Tetrazolo[1,5-a]pyridines
Further Information
Publication History
Received: 12 November 2012
Accepted: 27 November 2012
Publication Date:
12 December 2012 (online)
Abstract
This work describes a rapid and convenient synthesis of 3,5-disubstituted 2-chloropyridines from various α,β-unsaturated ketoximes utilizing the Vilsmeier reaction under microwave irradiation. The 3,5-disubstituted 2-chloropyridines were further converted into tetrazolo[1,5-a]pyridines by a microwave-mediated solid-phase reaction. The products were isolated in good yields within a very short reaction time.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Jones G. Comprehensive Heterocyclic Chemistry II . Vol. 5. Katritzky AR, Rees CW, Scriven EF. V. Pergamon; Oxford: 1996: 167
- 1b Balasubramanian M, Keay JG. Comprehensive Heterocyclic Chemistry II . Vol. 5. Katritzky AR, Rees CW, Scriven EF. V. Pergamon; Oxford: 1996: 245
- 1c Boger DL, Nakahara S. J. Org. Chem. 1991; 56: 880
- 2 Tian XT, Qin BJ, Lu H, Lai WH, Jiang SB, Lee KH, Chen CH, Xie L. Bioorg. Med. Chem. Lett. 2009; 19: 5482
- 3a Liu X.-H, Liu H.-F, Shen X, Song B.-A, Bhadury PS, Zhu H.-L, Liu J.-X, Qi X.-B. Bioorg. Med. Chem. Lett. 2010; 20: 4163
- 3b Pharmaceutical Chemistry: Drug Synthesis . Vol. 1. Roth HJ, Kleemann A. Prentice Hall Europe; London: 1988: 407
- 4 Matolcsy G. In Pesticide Chemistry. Nádasy M, Andriska V. Elsevier Scientific; Amsterdam: 1988: 427
- 5 Zheng Q.-Z, Zhang X.-M, Xu Y, Cheng K, Jiao Q.-C, Zhu H.-L. Bioorg. Med. Chem. 2010; 18: 7836
- 6 Narender P, Srinivas U, Gangadasu B, Biswas S, Rao VJ. Bioorg. Med. Chem. Lett. 2005; 15: 5378
- 7a Reichelt A, Falsey JR, Rzasa RM, Thiel OR, Achmatowicz MM, Larsen RD, Zhang D. Org. Lett. 2010; 12: 792
- 7b Maloney KM, Kuethe JT, Linn K. Org. Lett. 2011; 13: 102
- 7c Sonogashira K, Tohda Y, Hagihara N. Tetrahedron Lett. 1975; 16: 4467
- 7d Li G, Yang H, Li W, Zhang G. Green Chem. 2011; 13: 2939
- 8 Malkov AV, Pernazza D, Bell M, Bella M, Massa A, Teply F, Meghani P, Kocovsky P. J. Org. Chem. 2003; 68: 4727
- 9 Shen HC, Ding F.-X, Colletti SL. Org. Lett. 2006; 8: 1447
- 10a Simoni D, Rondanin R, Furno G, Aiello E, Invidiata FP. Tetrahedron Lett. 2000; 41: 2699
- 10b Pollak A, Polanc S, Stanovnik B, Tisler M. Monatsh. Chem. 1972; 103: 1591
- 10c Boyer JH, McCane DI, McCarville WJ, Tweedie AT. J. Am. Chem. Soc. 1953; 75: 5298
- 10d Mekheimer R. Pharmazie 1994; 49: 322
- 10e Reisinger A, Koch R, Wentrup C. J. Chem. Soc., Perkin Trans. 1 1998; 2247
- 10f Sasaki T, Kanematsu K, Murata M. Tetrahedron 1971; 27: 5359
- 11 Corkey B, Elzein E, Jiang R, Kalla R, Kobayashi T, Koltun D, Li X, Notte G, Parkhill E, Perry T, Zablocki J. US 20110021521, 2011
- 12 Chattopadhyay B, Rivera Vera CI, Chuprakov S, Gevorgyan V. Org. Lett. 2010; 12: 2166
- 13 Ahmed S, Boruah RC. Tetrahedron Lett. 1996; 37: 8231
- 14a Donohoe TJ, Basutto JA, Bower JF, Rathi A. Org. Lett. 2011; 13: 1036
- 14b Wang Q, Wan C, Gu Y, Zhang J, Gao L, Wang Z. Green Chem. 2011; 13: 578
- 15 Hutchinson JH, Stearns BA, Stock NS, Truong YP, Roppe JR, Volkots D, Scott JM, Parr TA, Wang B, Seiders TJ, Clark R, Coate HR. US 20110312974, 2011
- 16a Reddy KS, Iyengar DS, Bhalerao UT. Chem. Lett. 1983; 1745
- 16b Andrews DM, Page TC. M, Peach JM, Pratt AJ. J. Chem. Soc., Perkin Trans. 1 1995; 1045
- 16c Nishiyama K, Miyata I. Bull. Chem. Soc. Jpn. 1985; 58: 2419
- 16d Boyer JH, Schoen W. J. Am. Chem. Soc. 1956; 78: 423
- 16e Keith JM. J. Org. Chem. 2006; 71: 9540
- 17a Bora U, Saikia A, Boruah RC. Org. Lett. 2003; 5: 435
- 17b Gogoi S, Shekarrao K, Duarah A, Bora TC, Gogoi S, Boruah RC. Steroids 2012; 77: 1438; and references cited therein
- 18 Marson CM. Tetrahedron 1992; 48: 3659
- 19 Barthakur MG, Borthakur M, Boruah RC. Steroids 2008; 73: 1137