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

doi:10.1055/s-0028-1087990

PAPER

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

Roberta Bernini^a, Sandro Cacchi*^b, Giancarlo Fabrizi^b, Alessio Sferrazza^a
^a Dipartimento A.B.A.C., Università degli Studi della Tuscia e Consorzio Universitario ‘La Chimica per l’Ambiente’, Via S. Camillo De Lellis, 01100 Viterbo, Italy
^b Dipartimento di Chimica e Tecnologie del Farmaco, Università degli Studi ‘La Sapienza’, P.le A. Moro 5, 00185 Rome, Italy
Fax: +39(06)49912780; e-Mail: sandro.cacchi@uniroma1.it;

Abstract

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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 prepared via a sequential process from α,β-ynones and primary amines, omitting the isolation of the 1-(2-halophenyl)-2-en-3-amin-1-one intermediates.

Key words

copper - catalysis - enaminones - 4-quinolones - cyclizations

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Referenzen

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