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

Abdolhamid Alizadeh; Davood Nematollahi; Davood Hbibi; Mahdi Hesari

doi:10.1055/s-2007-966027

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

Abdolhamid Alizadeh*^a,b, Davood Nematollahi^c, Davood Hbibi^c, Mahdi Hesari^c
^a Department of Chemistry, Razi University, Kermanshah 67149, Iran
Fax: +98(831)4274559; e-Mail: ahalizadeh2@hotmail.com;
^b Nanoscience and Nanotechnology Research Center (NNRC), Razi University, Kermanshah 67149, Iran
^c Faculty of Chemistry, Bu-Ali Sina University, Hamadan 65174, Iran

Abstract

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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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