Y. Bulychev, I. A. Korbukh, M. Preobrazhenskaya
Feb 1, 1980
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Journal
Chemistry of Heterocyclic Compounds
Abstract
A number of 3,4,6-trisubstituted pyrazolo[3,4-d]pyrimidines and their 1-ribosides were synthesized from 3-cyano-4,6-dimethylmercaptopyrazolo [3,4-d]pyrimidine. The cyano group was converted to thiocarbamoyl, imido ester, carboxamidoximno, carboxamidrazono, carboxy, and amidino groups. The 4-methylmercapto group was replaced by mercapto, methoxy, amino, and hydrazino groups. The reactivities of methylmercapto and 3-cyano groups in substituted pyrazolo [3,4-d] pyrimidines and the corresponding nucleosides with respect to nucleophilic agents were compared. The introduction of a ribose residue in the 1 position facilitates nucleophilic addition to the 3-cyano group and replacement of the 4-methylmercapto group. High resistance of the 6-methylmercapto group to the action of nucleophilic agents and higher reactivity of the cyano groups as compared with methylmercapto groups were observed.