Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 11, Issue 20, Pages 2841-2845Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201601024
Keywords
[3+2] cycloaddition; 1,2-migration; imidazoles; isocyanides; silver
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Funding
- NSFC [21522202, 21502017, 21372038]
- Ministry of Education of the People's Republic of China [NCET-13-0714]
- Jilin Provincial Research Foundation for Basic Research [20140519008JH]
- Fundamental Research Funds for the Central Universities [2412015J005, 2412015KJ013]
- Jilin Province Key Laboratory of Organic Functional Molecular Design Synthesis [130028658]
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Imidazole ring is an important five-membered aromatic heterocycle that is widely present in natural products and synthetic molecules. The isocyanide-isocyanide [ 3+2] cross-cycloaddition reaction constitutes a straightforward method to access imidazoles starting from the easily available chemicals. So far, only three successive reports are known and all lead to the formation of 1,4-disubstituted imidazoles. Here, we report the first isocyanide-isocyanide [ 3+2] cross-cycloaddition reaction allowing for the formation of 1,4,5-trisubstituted imidazoles under silver catalysis. An unexpected 1,2-migration of sulfonyl, alkoxycaybonyl, and carbamoyl groups took place during the cyclization process that is responsible for the formation of trisubstituted imidazoles. This report displayed a mechanistically novel synthetic method toward a variety of imidazole derivatives, which are otherwise difficult to access by conventional methods.
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