Heterocyclic o-aminonitriles: Preparation of pyrazolo[3,4-d]-pyrimidines with modification of the substituents at the 1-position

Abstract

Novel 1-[6-(p-tolyl) pyridazin-3-yl]pyrazole-o-aminonitriles (3a-c) were formed using 3-hydrazino-6-(p-tolyl)pyridazine (2) and ketene S,S-acetals (1a), S,N-acetals (1b) or tetracyanoethylene (1c). The pyrazole-o-aminonitriles (3a-c) were in turn used as precursors for the preparation of previously unreported 1-[6-(p-tolyl)-pyridazin-3-yl]pyrazolo[3,4-d]pyrimidines (8, 9, 13-20) and 7-[6-(p-tolyl) pyridazin-3-yl]2-arylpyrazolo[3,4-d]1,2,4-triazolo[5,1-f] pyrimidines (10-12) which are expected to possess considerable chemical and pharmacological activities.