Bis-triazole Heterocycles as Antitubercular and Antimicrobial Agents: Synthesis Using Copper-Catalyzed Click Chemistry Approach

Piludiya, R. I.; Dholaria, Piyush; Jivani, Amita J.; Kapadiya, Khushal M.

doi:10.1134/s1070428022090135

Cited by 1 publication

(1 citation statement)

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“…Our group is continuously working to generate a new scaffold based on nitrogen-rich heterocycles and to identify lead in the thrust area of medicinal chemistry in which a real "Hitmen" like molecules are synthesized by applying hybridization of two or more active heterocycles concept [20][21][22][23][24]. Herein, we report the four-step synthetic strategy starting from easily accessible substrate, that is, methyl 3,4-diaminobenzoate to afford the high yielded regioselective adducts, 5-(5-amino-1H-pyrazol-3-yl)-1,-3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one derivatives (5a-l).…”

Section: Introductionmentioning

confidence: 99%

An efficient protocol for the synthesis of substituted 5‐amino pyrazole bearing benzo[d]imidazolone Core and their antioxidant activity

Sanghavi

Kher²,

Kapadiya

2023

Journal of Heterocyclic Chem

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An efficient, facile and regioselective route has been utilized for the synthesis of novel series of 5-(5-amino-1H-pyrazol-3-yl)-1,3-dimethyl-1,3-dihydro-2Hbenzo[d]imidazol-2-one derivatives (5a-l). The methyl 3,4-diaminobenzoate (1) used CDI/DMF system for the cyclization to benzimidazolone followed by Nmethylation and next ACN/n-BuLi media at À70 C to afford high yielded key intermediate, 3-(1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-3-oxopropanenitrile (4). The final adducts synthesis involved catalytic optimization to generate 5-amino pyrazole-based adducts (5a-l) rather than 3-amino pyrazole (6a-l) are discussed. Chromatographic and spectral techniques ( 1 H & 13C NMR, LC-MS, elemental analysis) confirmed the newly synthesized structures and were evaluated for antioxidant activity using DPPH free radical scavenging assay. The entire compounds showed extra (higher) potency against used standard ascorbic acid except 5j (2-F Ph substituent) while, 5c (ÀEt substitution) was found to be most potent among others.

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