In:
Chinese Journal of Chemistry, Wiley, Vol. 41, No. 17 ( 2023-09), p. 2089-2094
Abstract:
A domino ring‐opening and coupling of imidazolyl annulated heterocycles 1 ( 1a : 4‐methyl‐1‐(1‐methyl‐1 H ‐benzo[ d ]imidazol‐2‐yl)‐4 H ‐ benzo[ d ]imidazo[1,5‐ a ]imidazole, 1b : 1‐(1,5‐dimethyl‐1 H ‐benzo[ d ]imidazol‐2‐yl)‐4,7‐dimethyl‐4 H ‐benzo[ d ]imidazo[1,5‐ a ]imidazole) with dioxygen was developed at solvothermal condition, leading to conjugated 1,2‐diamidoalkenes derivatives 2 (( E )‐ArCONHArC=CArNHCOAr (Ar: 1‐methyl‐1 H ‐benzo[ d ]imidazolyl ( 2a ), 1,5‐dimethyl‐1 H ‐benzo[ d ]imidazolyl ( 2b ))) as single crystals directly. The reaction process was tracked by electrospray ionization mass spectrometry (ESI‐HRMS) and a series of reaction intermediates are detected. 18 O 2 labeling experiment verified the source of oxygen in 2 . Combining evidence from control experiments, nuclear magnetic resonance (NMR) tracking, and crystallography, a seven‐step reaction pathway involving oxygen addition, ring opening, Friedel‐Crafts alkylation, oxidation, and dehydration was proposed and further supported by DFT calculation.
Type of Medium:
Online Resource
ISSN:
1001-604X
,
1614-7065
DOI:
10.1002/cjoc.202300156
Language:
English
Publisher:
Wiley
Publication Date:
2023
detail.hit.zdb_id:
2144352-X
SSG:
6,25
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