Microwave-assisted Cu()-catalyzed one-pot tandem synthesis of pyridoimidazole-fused quinolines as new antimycobacterial agents: DFT and ESI-HRMS study

In this study, an improved microwave irradiation protocol was developed for synthesizing pyrido[2′,1′:2,3]imidazo[4,5- c ]quinoline from 2-(2-bromophenyl)imidazo[1,2- a ]pyridine and various benzaldehydes using copper iodide as a catalyst. This protocol also employed benzyl alcohols and methyl arene...

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Veröffentlicht in:New journal of chemistry 2023-03, Vol.47 (12), p.5961-5969
Hauptverfasser: Pawar, Gaurav, Ghouse, Shaik Mahammad, Joshi, Swanand Vinayak, Ahmad, Md Naiyaz, Dasgupta, Arunava, Yaddanapudi, Venkata Madhavi, Chopra, Siddharth, Nanduri, Srinivas
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Sprache:eng
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Zusammenfassung:In this study, an improved microwave irradiation protocol was developed for synthesizing pyrido[2′,1′:2,3]imidazo[4,5- c ]quinoline from 2-(2-bromophenyl)imidazo[1,2- a ]pyridine and various benzaldehydes using copper iodide as a catalyst. This protocol also employed benzyl alcohols and methyl arenes in addition to benzaldehyde. The proposed mechanism was supported by DFT and ESI-HRMS studies. Tandem oxidative addition, reductive amination, and intramolecular cyclization under microwave conditions result in the formation of new C-N and C-C bonds, respectively. Among the synthesized derivatives, compounds 3k , 3o , 3u , and 3w exhibited antimycobacterial activity against M. tuberculosis H37Rv ATCC 27294. An in silico ADMET profile was also performed to assess the active compound's safety and efficacy. One-pot tandem synthesis of diverse pyrido[2′,1′:2,3]imidazo[4,5- c ]quinolines as new antimycobacterial agents through a Cu( i )-catalyzed microwave-assisted protocol.
ISSN:1144-0546
1369-9261
DOI:10.1039/d2nj06165a