Issue 11, 2022

Tandem trifluoromethylthiolation and cyclization of N-aryl-3-butenamides with AgSCF3: divergent access to CF3S-substituted 3,4-dihydroquinolin-2-ones and azaspiro[4,5]dienones

Abstract

A AgSCF3-mediated tandem trifluoromethylthiolation and cyclization of N-aryl-3-butenamides was developed. It showed divergent reactivities and enabled the selective syntheses of CF3S-substituted 3,4-dihydroquinolin-2-ones and azaspiro[4,5]dienones. The selectivity was achieved through different cyclization pathways of a CF3S-substituted alkyl radical intermediate. It provides a useful tool for the synthesis of CF3S-substituted N-heterocyclic compounds.

Graphical abstract: Tandem trifluoromethylthiolation and cyclization of N-aryl-3-butenamides with AgSCF3: divergent access to CF3S-substituted 3,4-dihydroquinolin-2-ones and azaspiro[4,5]dienones

Supplementary files

Article information

Article type
Research Article
Submitted
08 Feb 2022
Accepted
21 Apr 2022
First published
22 Apr 2022

Org. Chem. Front., 2022,9, 3061-3067

Tandem trifluoromethylthiolation and cyclization of N-aryl-3-butenamides with AgSCF3: divergent access to CF3S-substituted 3,4-dihydroquinolin-2-ones and azaspiro[4,5]dienones

L. Wang, L. Xie, Z. Fang, Q. Zhang and D. Li, Org. Chem. Front., 2022, 9, 3061 DOI: 10.1039/D2QO00207H

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