N-Propargylic β-Enaminones: Common Intermediates for the Synthesis of Polysubstituted Pyrroles and Pyridines

Sandro Cacchi, Giancarlo Fabrizi and Eleonora Filisti

*Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Universit degli Studi “La Sapienza”, P.le A. Moro 5, 00185, Rome, Italy, Email: sandro.cacchiuniroma1.it

S. Cacchi, G. Fabrizi, E. Filisti, Org. Lett., 2008, 10, 2629-2632.

DOI: 10.1021/ol800518j

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Abstract

N-Propargylic β-enaminones are common intermediates for the synthesis of polysubstituted pyrroles and pyridines. In the presence of Cs₂CO₃ N-propargylic β-enaminones are cyclized to pyrroles in good to high yields, whereas CuBr leads to pyridines.

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Key Words

Pyrroles, Pyridines, β-Enaminones

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ID: J54-Y2008-1710