Synthesis of new pyrazole and antibacterial pyrazolopyrimidine derivatives

Abstract

3-Substituted-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amines 2a--c were synthesized by treating 5-aminopyrazole-4-carbonitriles 1a--c with formamide. The reactivity of compounds 1a--c towards some cyclic anhydrides was studied. The condensation of 5-aminopyrazole-4-carbonitrile 1b with triethylorthoformate gives imidate 7b, which reacts with a series of primary amines and leads to pyrazolo[3,4-d]pyrimidine-4-amines 9 and 10. The reaction of imidate 7b with ammonia and hydroxylamine afforded pyrazolopyrimidine 2b and pyrazolo[3,4-d]pyrimidin-5-(4H)-ol 11, respectively. The synthesized compounds were completely characterized by 1H NMR, 13C NMR, IR, and HRMS. The antibacterial activity of some new synthesized compounds was evaluated and appeared to be significant.