Regioselective Preparation of 1-(Bromomethyl)-5H-thiazolo[3,2-a]quinazolin-5-ones and Analogous 5H-Thieno[3,2-e]thiazolo[3,2-a]pyrimidin-5-ones from Fused 2-(Alkenylthio)pyrimidin-4-ones

Petra Wippich; Michael Gütschow; Siegfried Leistner

doi:10.1055/s-2000-6390

Synthesis 2000; 2000(5): 714-720
DOI: 10.1055/s-2000-6390

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Regioselective Preparation of 1-(Bromomethyl)-5H-thiazolo[3,2-a]quinazolin-5-ones and Analogous 5H-Thieno[3,2-e]thiazolo[3,2-a]pyrimidin-5-ones from Fused 2-(Alkenylthio)pyrimidin-4-ones

Petra Wippich^* , Michael Gütschow, Siegfried Leistner

^*Institut für Pharmazie - Pharmazeutische Chemie - der Universität Leipzig, Brüderstr. 34, D-04103 Leipzig, Germany; Fax + 49(341)0 73 67 49; E-mail: guetscho@uni-leipzig.de

Abstract

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A convenient procedure for the regioselective preparation of polycyclic angular thiazolo[3,2-a]pyrimidin-5-ones is reported. 2-(Alkenylthio)quinazolin-4(3H)-ones and analogues thieno[2,3-d]pyrimidines were treated with bromine in acetic acid to obtain 1-(bromomethyl)-5H-thiazolo[3,2-a]quinazolin-5-ones 8a,d, and 1-(bromomethyl)-5H-thieno[3,2-e]thiazolo[3,2-a]pyrimidin-5-ones 8b,c,e,f, respectively. A route starting from 2-(alkenylamino)benzamides, which were converted to corresponding 2-thioxoquinazolin-4-ones and subsequently treated with bromine in acetic acid furnished angular 2-(bromomethyl)thiazolo[3,2-a]quinazolin-5-ones 11, or 3-(bromomethyl)[1,3]thiazino[3,2-a]quinazolin-6-ones 14, respectively.

polycyclic pyrimidinones - thiazolo[3,2-a]quinazolin-5-ones - thieno[3,2-e]thiazolo[3,2-a]pyrimidin-5-ones - bromocyclization - 2-(alkenylthio)pyrimidin-4-ones - heterocycles

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