Turkish Journal of Chemistry
DOI
10.3906/kim-1303-20
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.
Keywords
Aminopyrazoles, pyrimidines, maleic anhydride, pyrazolo[3, 4-d]pyrimidines, Dimroth rearrangement, antibacterial activity
First Page
210
Last Page
221
Recommended Citation
RAHMOUNI, AMEUR; ROMDHANE, ANIS; SAID, ABDERRAHIM BEN; MAJOULI, KAOUTHER; and JANNET, HICHEM BEN
(2014)
"Synthesis of new pyrazole and antibacterial pyrazolopyrimidine derivatives,"
Turkish Journal of Chemistry: Vol. 38:
No.
2, Article 5.
https://doi.org/10.3906/kim-1303-20
Available at:
https://journals.tubitak.gov.tr/chem/vol38/iss2/5
