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Synthesis 2009(3): 438-444  
DOI: 10.1055/s-0028-1083318
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Three-Step Synthesis of Pyrazinothienopyrimidines Using Tandem Aza-Wittig/Electrocyclic Ring Closure

Gerardo Blanco, Antonio Fernández-Mato, José M. Quintela*, Carlos Peinador*
Departamento de Química Fundamental, Facultad de Ciencias, Universidad de A Coruña, 15071 A Coruña, Spain
Fax: +34(981)167000; e-Mail: jqqoqf@udc.es; capeveqo@udc.es;
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Publication History

Received 7 July 2008
Publication Date:
09 January 2009 (online)

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Abstract

A facile and efficient one-pot procedure for the preparation of pyrazino[3′,2′:4,5]thieno[3,2-d]pyrimidines following a tandem aza-Wittig/electrocyclic ring closure strategy is described. The one-pot, three-step reaction between 3-amino-2-formylthieno[2,3-b]pyrazine, primary amines, dichlorotriphenylphosphine and heterocumulenes, proceeded effectively and the yields of the products were higher than in the stepwise process. The products can also be prepared directly by a one-pot, two-step reaction using the same aldehyde, dichlorotriphenylphosphine and isocyanates. The advantages of the present method are easily accessible starting materials, experimental simplicity of the one-pot procedure, and good yields.

Key words

heterocycles - Wittig reaction - electrocyclic reactions - phosphazenes - cyclizations

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Crystallographic data (excluding structure factors) for 6f has been deposited with the Cambridge Crystallographic Data Center as supplementary publication number CCDC 692136. Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44(1223)33603 or e-mail: deposit@ccdc.cam.ac.uk].