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E-Journal of Chemistry
Volume 9 (2012), Issue 1, Pages 219-223
http://dx.doi.org/10.1155/2012/762641

Synthesis of Novel 6-Cyano-9-(aryl)-9H-purine Derivatives Via Formamidine Intermediates

Hashemi Seyyed Milad,1 Yahyazadeh Asieh,1 and Nami Navabeh2

1Department of Chemistry, Guilan University, P.O. Box 1914, Rasht, Guilan, Iran
2Department of Chemistry, Islamic Azad University, Qaemshahr, Mazandaran, Iran

Received 19 August 2010; Accepted 20 October 2010

Copyright © 2012 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Novel 9-substituted cyanopurine derivatives (4a-d) were synthesized in three steps in high yield. Diaminomaleonitrile (1) reacted with triethyl orthoformate to afford (Z)-N-[2-amino-1,2-dicyanovinyl] formimidate (2) which was converted to aryl-(Z)-N-[2-amino-1,2-dicyanovinyl] formamidines (3a-d) in the presence of a catalytic amount of anilinium chloride and aromatic amines in ethanol at room temperature under inert atmosphere (Argon). Furthermore, the reaction of (3a-d) with triethyl orthoformate afforded novel 6-cyano-9-(aryl)-9H-purine derivatives (4a-d) which can be used without further purification. All compounds have been fully characterized by spectroscopic data.