Author/Authors :
RAHMOUNI, Ameur University of Monastir - Monastir Faculty of Science - Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity, Medicinal Chemistry and Natural Products, Tunisia , ROMDHANE, Anis University of Monastir - Monastir Faculty of Science - Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity, Medicinal Chemistry and Natural Products, Tunisia , BEN SAID, Abderrahim University of Monastir - Monastir Faculty of Science - Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity, Medicinal Chemistry and Natural Products, Tunisia , MAJOULI, Kaouther University of Monastir - Faculty of Medicine - Laboratory of Biochemistry, Molecular Mechanisms, and Pathologies, Tunisia , BEN JANNET, Hichem University of Monastir - Monastir Faculty of Science - Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity, Medicinal Chemistry and Natural Products, Tunisia
Abstract :
3-Substituted-1-phenyl-1 H -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-(4 H) -ol 11, respectively. The synthesized compounds were completely characterized by 1 H NMR, 13 C NMR, IR, and HRMS. The antibacterial activity of some new synthesized compounds was evaluated and appeared to be significant.
Keywords :
Aminopyrazoles , pyrimidines , maleic anhydride , pyrazolo[3 , 4 , d ]pyrimidines , Dimroth rearrangement , antibacterial activity
