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Ts 2 O Promoted Deoxygenative C-H Dithiocarbonation of Quinoline N -Oxides with Potassium O -Alkyl Xanthates.

Authors :
Zhao MY
Tang JJ
Lin YJ
Tian ZY
Peng S
Xie LY
Source :
The Journal of organic chemistry [J Org Chem] 2024 Apr 19; Vol. 89 (8), pp. 5560-5572. Date of Electronic Publication: 2024 Apr 02.
Publication Year :
2024

Abstract

A simple, efficient, and practical method for the synthesis of S-quinolyl xanthates was developed via Ts <subscript>2</subscript> O-promoted deoxygenative C-H dithiocarbonation of quinoline N-oxides with various potassium O-alkyl xanthates. The reaction performed well under transition-metal-free, base-free, and room-temperature conditions with wide substrate tolerance. Employing potassium O - tert -butyl xanthate ( <superscript>t</superscript> BuOCS <subscript>2</subscript> K) as a nucleophile, some valuable quinoline-2-thiones were unexpectedly obtained in a one-pot reaction without any additional base.

Details

Language :
English
ISSN :
1520-6904
Volume :
89
Issue :
8
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
38564232
Full Text :
https://doi.org/10.1021/acs.joc.4c00031