Affiliation:
1. State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China) Collaborative Innovation Center for Guangxi Ethnic Medicine; School of Chemistry and Pharmaceutical Sciences Guangxi Normal University 15 Yu Cai Road Guilin 541004 People's Republic of China
2. Key Laboratory of Chemistry and Engineering of Forest Products State Ethnic Affairs Commision Guangxi Key Laboratory of Chemistry and Engineering of Forest Products Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products School of Chemistry and Chemical Engineering Guangxi Minzu University Nanning 530008 People's Republic of China
Abstract
AbstractWe described a base‐promoted O‐arylation of N3‐hydroxyl quinazolinones with diaryliodonium salts and sequential BF3 ⋅ OEt2 and visible light‐controlled [3,3]‐ or [1,3]‐rearrangements of quinazolinone N−O aryl moieties to prepare a variety of 2‐(quinazolin‐4‐yloxy)phenols and atropisomeric 3‐(2‐hydroxyphenyl)quinazolin‐4‐ones in 44%‐75% yields and 28%‐70% yields, respectively. Mechanistic studies showed that HBF4 generated in situ from BF3 ⋅ Et2O and water served as the catalyst in this process and aryloxyquinazolinium salts are vital intermediates promoting the [3,3]‐ or [1,3]‐rearrangements. The N−O aryl moieties of aryloxyquinazolinium salts were found to undergo solely [3,3]‐rearrangement with heating whereas [1,3]‐rearrangement occurred via a radical process under irradiation of visible light. This method highlights the formation of aryloxyquinazolinium salts based on the use of BF3 ⋅ OEt2 and visible light to prompt [1,3]‐rearrangement generating atropisomeric quinazolinones.
Funder
National Natural Science Foundation of China
Cited by
1 articles.
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