Tetrahedron

A regiospecific synthesis of 2-azaanthraquinon-3-ones via a hetero Diels-Alder reaction with bromonaphthoquinones

B Bouammali, F Pautet, H Fillion, M Soufiaoui

Index: Bouammali; Pautet; Fillion; Soufiaoui Tetrahedron, 1993 , vol. 49, # 15 p. 3125 - 3130

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Citation Number: 14

Abstract

The Diels-Alder reaction 2-azadienes and 2-or 3-bromo-5-substituted naphthoquinones (R3= OH, OAc, OMe) led to a regiospecific synthesis of the corresponding 2- azaanthraquinones-3-ones. The results indicate that the bromine atom exerts a stronger regiochemical control in these cycloaddition than the 5-substituent.