An efficient method for the synthesis of [1,4]thiazino[4,3-]indole derivatives using sodium chlorodifluoroacetate (ClCFCONa) and elemental sulfur as the difluoromethylthiolating reagent system has been developed. Three-component reactions of 2'-aminochalcones, sulfur, and ClCFCONa under basic conditions using TEMPO as the oxidant afforded [1,4]thiazino[4,3-]indol-10-ones containing a difluoromethyl thioether moiety in good yields. Four bonds including one C-N, two C-S, and one C-C bonds are selectively formed in the sequential transformation process.
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Synthesis of [1,4]Thiazino[4,3-]indol-10-one Derivatives through Radical Anti Aza-Michael Addition of 2'-Aminochalcones.
Org Lett
August 2021
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, China.
An efficient method for the synthesis of [1,4]thiazino[4,3-]indole derivatives using sodium chlorodifluoroacetate (ClCFCONa) and elemental sulfur as the difluoromethylthiolating reagent system has been developed. Three-component reactions of 2'-aminochalcones, sulfur, and ClCFCONa under basic conditions using TEMPO as the oxidant afforded [1,4]thiazino[4,3-]indol-10-ones containing a difluoromethyl thioether moiety in good yields. Four bonds including one C-N, two C-S, and one C-C bonds are selectively formed in the sequential transformation process.
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