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BF3 ⋅ OEt2 and Visible Light‐Controlled [3,3]‐ or [1,3]‐Rearrangement of Quinazolinone N−O Aryl Moieties.
- Source :
- Advanced Synthesis & Catalysis; 5/21/2024, Vol. 366 Issue 9, p2056-2062, 7p
- Publication Year :
- 2024
-
Abstract
- We 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. [ABSTRACT FROM AUTHOR]
- Subjects :
- QUINAZOLINONES
MOIETIES (Chemistry)
VISIBLE spectra
Subjects
Details
- Language :
- English
- ISSN :
- 16154150
- Volume :
- 366
- Issue :
- 9
- Database :
- Complementary Index
- Journal :
- Advanced Synthesis & Catalysis
- Publication Type :
- Academic Journal
- Accession number :
- 177377934
- Full Text :
- https://doi.org/10.1002/adsc.202301345