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1,2-Disubstituted 4-Quinolones via Copper-Catalyzed Cyclization of 1-(2-Halophenyl)-2-en-3-amin-1-ones

Roberta Bernini, Sandro Cacchi*, Giancarlo Fabrizi, Alessio Sferrazza

*Dipartimento di Chimica e Tecnologie del Farmaco, UniversitÓ degli Studi ‘La Sapienza', P.le A. Moro 5, 00185 Rome, Italy, Email: sandro.cacchiuniroma1.it

R. Bernini, S. Cacchi, G. Fabrizi, A. Sferrazza, Synthesis, 2009, 1209-1219.

DOI: 10.1055/s-0028-1087990


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Abstract

1,2-Disubstituted 4-quinolones have been prepared via copper-catalyzed heterocyclization of 1-(2-bromophenyl)- and 1-(2-chlorophenyl)-2-en-3-amin-1-ones, readily obtained from α,β-ynones and primary amines. The reaction tolerates a variety of useful functionalities including ester, keto, cyano, and chloro substituents. Quinolone derivatives can also be directly prepared from α,β-ynones.

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Key Words

copper, catalysis, enaminones, 4-quinolones, cyclizations


ID: J66-Y2009-1170