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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 1
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Original Articles

Copper Bromide–Catalyzed C-Alkylation of 2-Amino-1,4-Naphthoquinone: New Synthesis of 1-Azaanthraquinones

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Pages 151-156 | Received 27 Jan 2009, Published online: 09 Dec 2009
 

Abstract

Copper(I) bromide catalyzes the regioselective Michael addition reaction of 2-amino-1,4-naphthoquinone (5) with methyl vinyl ketone and 2-propenal to provide easy access to C-alkylated quinone derivatives, useful precursors of 1-azaanthraquinones.

ACKNOWLEDGMENTS

We are grateful to Fondo Nacional de Desarrollo Científico y Tecnológico (FONDECYT, Research Grant 1060592) and Comisión Nacional de Investigación Científica y Tecnológica (CONICYT, fellowship to L. C. and Research Grant AT24080019).

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