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 2012; 44(21): 3301-3306
DOI: 10.1055/s-0032-1317178
DOI: 10.1055/s-0032-1317178
paper
Copper-Catalyzed Selective Synthesis of Highly Substituted Pyridones by the Reaction of Enaminones with Alkynes
Further Information
Publication History
Received: 16 July 2012
Accepted after revision: 10 August 2012
Publication Date:
23 August 2012 (online)

Abstract
An efficient copper-catalyzed selective synthesis of highly functionalized pyridones by the reaction of enaminones with alkynes is reported. The reactions proceed to afford polysubstituted pyridone derivatives in good to high yields using CuI as the catalyst in MeCN under nitrogen.
Key words
copper catalysis - pyridones - regioselective cyclization - enaminones - cascade reactionsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Baxendale IR, Ley SV, Piutti C. Angew. Chem. Int. Ed. 2002; 41: 2194
- 1b Varela JA, Saa C. Chem. Rev. 2003; 103: 3787
- 1c Wolkenberg SE, Boger DL. J. Org. Chem. 2002; 67: 7361
- 2a Nakamura I, Yamamoto Y. Chem. Rev. 2004; 104: 2127
- 2b Torres M, Gil S, Parra M. Curr. Org. Chem. 2005; 9: 1757
- 2c Rigby JH. Synlett 2000; 1
- 3a Imase H, Noguchi K, Hirano M, Tanaka K. Org. Lett. 2008; 10: 3563
- 3b Takahashi T, Tsai F-Y, Li Y, Wang H, Kondo Y, Yamanaka M, Nakajima K, Kotora M. J. Am. Chem. Soc. 2002; 124: 5059
- 3c Schirok H, Alonso-Alija C, Benet-Buchholz J, Goller AH, Grosser R, Michels M, Paulsen H. J. Org. Chem. 2005; 70: 9463
- 3d Chun YS, Ryu KY, Ko YO, Hong JY, Hong J, Shin H, Lee S. J. Org. Chem. 2009; 74: 7556
- 3e Wang M.-X, Miao W.-S, Cheng Y, Huang Z.-T. Tetrahedron 1999; 55: 14611
- 3f Duong HA, Cross MJ, Louie J. J. Am. Chem. Soc. 2004; 126: 11438
- 3g Schirok H, Alonso-Alija C, Benet-Buchholz J, Goller AH, Grosser R, Michels M, Paulsen H. J. Org. Chem. 2005; 70: 9463
- 3h Duong HA, Louie J. Tetrahedron 2006; 62: 7552
- 4a Stanovnik B, Svete J. Chem. Rev. 2004; 104: 2433
- 4b Elassar A-ZA, El-Khair AA. Tetrahedron 2003; 59: 8463
- 5a Wurtz S, Rakshit S, Neumann JJ, Droge T, Glorius F. Angew. Chem. Int. Ed. 2008; 47: 7230
- 5b Neumann JJ, Suri M, Glorius F. Angew. Chem. Int. Ed. 2010; 49: 7790
- 5c Bernini R, Fabrizi G, Sferrazza A, Cacchi S. Angew. Chem. Int. Ed. 2009; 48: 8078
- 5d Neumann JJ, Rakshit S, Droge T, Wurtz S, Glorius F. Chem. Eur. J. 2011; 17: 7298
- 5e Yang J, Wang C, Xie X, Li H, Li Y. Eur. J. Org. Chem. 2010; 4189
- 5f Peruncheralathan S, Yadav AK, Ila H, Junjappa H. J. Org. Chem. 2005; 70: 9644
- 5g Yan R.-L, Luo J, Wang C.-X, Ma C-W, Huang G-S, Liang Y-M. J. Org. Chem. 2010; 75: 5395
- 5h Vohra RK, Bruneau C, Renaud J.-L. Adv. Synth. Catal. 2006; 348: 2571
- 6a Savarin CG, Murry JA, Dormer PG. Org. Lett. 2002; 4: 2071
- 6b Ali AA, Winzenberg KN. Aust. J. Chem. 2005; 58: 870
- 7 Cacchi S, Fabrizi G, Filisti E. Org. Lett. 2008; 10: 2629
- 8a Yang J, Wang C, Xie X, Li H, Li Y. Eur. J. Org. Chem. 2010; 4189
- 8b Yang J, Wang C, Xie X, Li H, Li E, Li Y. Org. Biomol. Chem. 2011; 9: 1342
- 8c Li E, Yao W, Xie X, Wang C, Shao Y, Li Y. Org. Biomol. Chem. 2012; 10: 2960
- 9 CCDC 861423 contains the supplementary crystallographic data of 3a for this paper. This data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; E-mail: deposit@ccdc.cam.ac.uk
For reviews, see:
For reviews, see:
For recent examples, see: