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Tracking the Process of Domino Ring‐Opening and Coupling of Fused Imidazole and Direct Observation of Peroxide Intermediates.
- Source :
-
Chinese Journal of Chemistry . Sep2023, Vol. 41 Issue 17, p2089-2094. 6p. - Publication Year :
- 2023
-
Abstract
- Comprehensive Summary: A domino ring‐opening and coupling of imidazolyl annulated heterocycles 1 (1a: 4‐methyl‐1‐(1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)‐4H‐ benzo[d]imidazo[1,5‐a]imidazole, 1b: 1‐(1,5‐dimethyl‐1H‐benzo[d]imidazol‐2‐yl)‐4,7‐dimethyl‐4H‐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‐1H‐benzo[d]imidazolyl (2a), 1,5‐dimethyl‐1H‐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. 18O2 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 1001604X
- Volume :
- 41
- Issue :
- 17
- Database :
- Academic Search Index
- Journal :
- Chinese Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 169706983
- Full Text :
- https://doi.org/10.1002/cjoc.202300156