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Paper | Regular issue | Vol 36, No. 10, 1993, pp.2281-2290
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6416
Synthesis with Nitriles: 92. Synthesis of 5-Formylcytosine Derivatives

Madhukar Jachak,* Martin Mittelbach, and Hans Junek

*Institute for Organic Chemistry,University Graz, Heinrichstrbe. 28, A-8010 Graz, Austria

Abstract

The reactivity of 3-dimethylamino-2-formylpropenenitrile (1) with various amino compounds is studied. Thus, condensation of 1 with anilines gives the corresponding azomethines (2a-c). Reaction of 1 with thiourea and guanidine resp., leads to 5-formylthiocytosine (3) and 2-amino-5-cyanopyrimidine (4). The 2-formyl-3-ureidopropenenitriles (5a-i) can be obtained by reaction of 1with urea and substituted ureas. 5a-i can easily be cyclized to 3-substituted 5-formylcytosines (6a-e). Condensation of 6 with aniline, benzylamine and phenylhydrazine leads to the azomethines (7a-i). Pyrido[2,3-d]pyrimidine-6-carbonitriles (8a, 8b, 8d and 8e) are obtained by reaction of 6 with malononitrile.