Synthesis of 6-cyano and 6-unsubstituted 2-aryl-8-oxopurine from a common 2-oxoimidazole precursor

Magdi E. A. Zaki; M. Fernanda Proenca

doi:10.1016/j.tet.2010.11.064

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Synthesis of 6-cyano and 6-unsubstituted 2-aryl-8-oxopurine from a common 2-oxoimidazole precursor

Journal article

Peer reviewed

Synthesis of 6-cyano and 6-unsubstituted 2-aryl-8-oxopurine from a common 2-oxoimidazole precursor

Magdi E. A. Zaki and M. Fernanda Proenca

Tetrahedron, Vol.67(4), pp.755-762

28/01/2011

DOI: https://doi.org/10.1016/j.tet.2010.11.064

Abstract

Chemistry

Chemistry, Organic

Physical Sciences

Science & Technology

The benzyl urea of diaminomaleonitrile, prepared from commercially available starting materials, was reacted with aromatic aldehydes at room temperature. Intramolecular cyclization of the product, in basic solution, generated a substituted 2-oxoimidazole. This compound proved to be a common precursor for 2-aryl-6-cyano-8-oxopurines upon treatment with acid and for 2-aryl-6-unsubstituted-8-oxopurines, in the presence of base. A H-1 NMR study of these simple and versatile reactions supports the mechanistic proposal. (C) 2010 Published by Elsevier Ltd.

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Details

Title: Synthesis of 6-cyano and 6-unsubstituted 2-aryl-8-oxopurine from a common 2-oxoimidazole precursor
Creators - without role: Magdi E. A. Zaki - University of Minho
M. Fernanda Proenca - University of Minho
Publication Details: Tetrahedron, Vol.67(4), pp.755-762
Publisher: Elsevier
Number of pages: 8
Grant note: University of Minho SFRH/BPD/27029/2006 / Fundao para a Cincia e a Tecnologia SFRH/BPD/27029/2006 / Fundacao para a Ciencia e Tecnologia; Fundacao para a Ciencia e a Tecnologia (FCT)
Identifiers: 9916257908331
Academic Unit: Imam Mohammad Ibn Saud Islamic University (IMSIU)
Language: English
Resource Type: Journal article