N-propargylic beta-enaminones: common intermediates for the synthesis of polysubstituted pyrroles and pyridines.

Org Lett

Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università degli Studi La Sapienza, P.le A. Moro 5, 00185, Rome, Italy.

Published: July 2008

N-Propargylic beta-enaminones have been used as common intermediates for the synthesis of polysubstituted pyrroles and pyridines. Best results have been obtained using DMSO as solvent. In the presence of Cs(2)CO(3) N-propargylic beta-enaminones are cyclized to pyrroles in good to high yields, whereas omitting bases and using CuBr leads to the selective formation of pyridines.

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http://dx.doi.org/10.1021/ol800518jDOI Listing

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