Abstract
Comprehensive SummaryA 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.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.