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Synfacts 2010(11): 1222-1222
DOI: 10.1055/s-0030-1258760
DOI: 10.1055/s-0030-1258760
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed Synthesis of Poly-substituted Pyrroles from Enamino Ketones
R.-L. Yan, J. Luo, C.-X. Wang, C.-W. Ma, G.-S. Huang*, Y.-M. Liang*
Lanzhou University, P. R. of China
Further Information
Publication History
Publication Date:
21 October 2010 (online)
Significance
Reported is an efficient method for the synthesis of polysubstituted pyrroles from oxidative cyclization of β-enamino ketones with alkynoates catalyzed by CuI. Based on previous results (Y. Liang and co-workers Synlett 2010, 1071), oxygen was found to be the most efficient oxidant for this reaction. The scope was investigated with a variety of substituted β-enamino ketones or esters 1. The yields of product 3 are much lower for R³ = EDG than for R³ = EWG. A wide range of N-substituents are tolerated. A plausible mechanism was proposed without evidence.