Domino Oxidation-Michael Reactions of Catechols with Barbituric Acid Derivatives in Water: An Efficient Synthesis of Polycyclic Pyrimidinones

Abstract

The oxidative coupling reaction of catechols with barbituric acid derivatives, mediated by ferricyanide, has been investigated in aqueous solution. The results indicate that the barbituric acid derivatives participate in Michael-type addition reactions with in situ generated ortho-benzoquinones, in a domino fashion, to afford a variety of polycyclic pyrimidinones. The method provides a one-step, rapid and efficient procedure for synthesizing a range of polycyclic pyrimidinones of biological significance.

Key words

catechols - quinines - Michael additions - domino reactions - polycycles

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