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Paper | Regular issue | Vol 71, No. 9, 2007, pp.1951-1966
Published online, 15th June, 2007
DOI: 10.3987/COM-07-11083
Utility of Cyanoacetamides as Precursors to Pyrazolo[3,4-d]pyrimidin-4-ones, 2-Aryl-6-substituted 1,2,3 Triazolo[4,5-d]pyrimidines and Pyrazolo[1,5-a]pyrimidine-3-carboxamides

Hamada Mohamed Ibrahim, Saad Makhseed,* Ramadan Maawad Abdel-Motaleb, Abdel-Moneim Abdel-Salam Makhlouf, and Mohamed Hilmy Elnagdi

*Chemistry Department, Faculty of Science, Kuwait University, Kuwait, P.O. Box, 5969 Safate 13060, State of Kuwait

Abstract

Cyanoacetamides (7a-c) were prepared via reacting cyanoacetic acid (5) with amines in the presence of acetic anhydride. Compounds (7a-c) coupled with benzenediazonium chloride to yield the phenylhydrazones (8a-c). These reacted with chloroacetonitrile to yield aminopyrazolecarboxamides (11a-c). Reaction of (8a,b) with hydroxylamine hydrochloride in DMF in presence of anhydrous sodium acetate afforded the amino-1,2,3-triazolecarboxamides (36a,b). Also compounds (7a-c) reacted with dimethylformamide dimethylacetal (DMFDMA) to yield the enamines (9a-c) which react with hydrazine hydrate to afford the aminopyrazoles (16a-c). Compounds (16) and (36) reacted with DMFDMA to yield the title heterocyclic derivatives.