Turkish Journal of Chemistry
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, ^{13}C NMR, IR, and HRMS. The antibacterial activity of some new synthesized compounds was evaluated and appeared to be significant.
DOI
10.3906/kim-1303-20
Keywords
Aminopyrazoles, pyrimidines, maleic anhydride, pyrazolo[3, 4-d]pyrimidines, Dimroth rearrangement, antibacterial activity
First Page
210
Last Page
221
Recommended Citation
RAHMOUNI, A, ROMDHANE, A, SAID, A. B, MAJOULI, K, & JANNET, H. B (2014). Synthesis of new pyrazole and antibacterial pyrazolopyrimidine derivatives. Turkish Journal of Chemistry 38 (2): 210-221. https://doi.org/10.3906/kim-1303-20
