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 |
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Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
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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. |
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ISSN: | 1144-0546 1369-9261 |
DOI: | 10.1039/d2nj06165a |