Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 19, Pages 4058-4063Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob00040e
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Funding
- Natural Science Foundation of China [21272077, 21402014, 21672027]
- QingLan Project of Jiangsu Province
- Six-Talent-Peaks Program of Jiangsu
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There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with arynes, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into the thiocarbonyl group (C=S). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazoles. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with arynes, it is found that N-arylation outcompetes O-arylation and aryne insertion into the C=O group to give N-aryl 2-benzoxazolinones and N-aryl 2-benzimidazolinones.
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