953390-07-3Relevant articles and documents
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
Ibrahim, Hamada Mohamed,Makhseed, Saad,Abdel-Motaleb, Ramadan Maawad,Makhlouf, Abdel-Moneim Abdel-Salam,Elnagdi, Mohamed Hilmy
, p. 1951 - 1966 (2007)
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.