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Paper | Regular issue | Vol 41, No. 6, 1995, pp.1169-1179
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6999
Diels-Alder Reactions of a Hydrazonocrotonate with Bromonaphthoquinones

Leila Chaker, Félix Pautet, and Houda Fillion*

*Laboratoire de Chimie Organique, Institut des Sciences Pharmaceutiques et Biologiques, Université Claude Bernard, 8 avenue Rockefeller, 69373 Lyon Cedex 08, France

Abstract

An efficient and regiospecific synthesis of 4,6- and 4,9-disubstituted 5,10-benzo[g]quinolinequinone derivatives was performed through a hetero Diels-Alder reaction between methyl (E)-4-dimethylhydrazono-2-butenoate (1) and 2- or 3-bromo-5-substituted naphthoquinones (2) and (3). According to the experimental conditions used, the corresponding dihydro or aromatic compounds were isolated as the major products. The regiochemistry of the cycloadditions is governed by the position of the bromine atom C-2 or C-3 of the quinone.