Ameur RAHMOUNI, Anis ROMDHANE, Abderrahim Ben SAID, Kaouther MAJOULI, Hichem BEN JANNET

Synthesis of new pyrazole and antibacterial pyrazolopyrimidine derivatives

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.

Anahtar Kelimeler:

Aminopyrazoles, pyrimidines, maleic anhydride, pyrazolo[3, 4-d]pyrimidines, Dimroth rearrangement, antibacterial activity

Synthesis of new pyrazole and antibacterial pyrazolopyrimidine derivatives

Keywords:

Aminopyrazoles, pyrimidines, maleic anhydride, pyrazolo[3, 4-d]pyrimidines, Dimroth rearrangement, antibacterial activity,

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