TsCl promoted deoxygenative phosphorothiolation of quinoline -oxides towards -quinolyl phosphorothioates

A convenient, efficient and practical approach for the synthesis of S -quinolyl phosphorothioates via cheap TsCl promoted deoxygenative C2-H phosphorothiolation of quinoline N -oxides with readily available triethylammonium O , O -dialkylphosphorothioates was developed. The reaction performed well u...

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Published in:Organic & biomolecular chemistry 2024-03, Vol.22 (12), p.249-2413
Main Authors: Wu, Li-Yao, Tian Huang, Tian, Zhong-Ying, Xu, Xiang-Qin, Peng, Sha, Xie, Long-Yong
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Summary:A convenient, efficient and practical approach for the synthesis of S -quinolyl phosphorothioates via cheap TsCl promoted deoxygenative C2-H phosphorothiolation of quinoline N -oxides with readily available triethylammonium O , O -dialkylphosphorothioates was developed. The reaction performed well under transition-metal-free conditions at room temperature with a very short reaction time (10-20 min). Preliminary studies showed that the current transformation underwent a nucleophilic substitution process. TsCl promoted deoxygenative C2-H phosphorothiolation of quinoline N -oxides with triethylammonium O , O -dialkylphosphorothioates towards various S -quinolyl phosphorothioates was developed.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00111g