Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 24, Pages 16204-16212Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01680
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Funding
- Natural Science Foundation of Anhui Province [2008085QB64]
- Foundation of Anhui Province Key Laboratory of Clean Energy Materials and Chemistry for Sustainable Conversion of Natural Resources [LCECSC-15]
- Foundation of China National Tobacco Corporation [110201903003]
- Foundation of Anhui Polytechnic University [Xjky2020079]
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An iodine-promoted domino reaction method has been discovered, which allows for the efficient synthesis of a variety of 1,2,4-trisubstituted 5-(o-hydroxybenzoyl)imidazoles. The reaction proceeds in a consecutive manner, involving Michael addition, iodination, cyclization from intramolecular nucleophilic substitution, and dehydrogenative aromatization from spiro ring opening.
An iodine-promoted domino reaction of aurones with amidines has been successfully explored. The reaction proceeds in a consecutive manner containing Michael addition, iodination, cyclization from intramolecular nucleophilic substitution, and dehydrogenative aromatization from spiro ring opening. Following this novel strategy, a variety of 1,2,4-trisubstituted 5-(o-hydroxybenzoyl)imidazoles were efficiently synthesized in moderate to good yields from readily available starting materials. A plausible mechanism has been proposed.
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