Synthesis of Pyrazinothienopyrimidine Derivatives by the Application of the Intramolecular and Intermolecular Aza-Wittig Reaction/Heterocyclization

Abstract

Pyrazino[2′,3′:4,5]thieno[3,2-d]pyrimidine derivatives 6 were synthesized by the intermolecular aza-Wittig reaction of N-heteroaryl phosphazene derivatives with carboxylic acid chlorides. The heterocyclization occurs via imidoyl chloride intermediates derived from phosphazenes 4a,b, obtained in a one-step process from α-azidothieno[2,3-b]pyrazine carboxylic acid 3. Moreover, cyclic pyrazinothienopyrimidines were prepared, in a two-step procedure, from amides and azidothienopyrazine-α-carbonyl chloride using an intramolecular aza-Wittig heterocyclization reaction strategy.

heterocycles - Wittig reaction - nitrogen - azides - cyclizations

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Crystallographic data (excluding structure factors) for 6b and 9a have been deposited with the Cambridge Crystallographic Data Center as supplementary publication numbers 6b: CCDC 668435, and 9a: CCDC 668436. Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: [phone] or e-mail: [e-mail]).

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