Synthesis of [1,4]Thiazino[4,3-<i>a</i>]indol-10-one Derivatives through Radical Anti Aza-Michael Addition of 2′-Aminochalcones
Pingshun Zhang, Linjie Yang, Wanzhi Chen, Miaochang Liu, Huayue Wu
Abstract
An efficient method for the synthesis of [1,4]thiazino[4,3-a]indole derivatives using sodium chlorodifluoroacetate (ClCF2CO2Na) and elemental sulfur as the difluoromethylthiolating reagent system has been developed. Three-component reactions of 2′-aminochalcones, sulfur, and ClCF2CO2Na under basic conditions using TEMPO as the oxidant afforded [1,4]thiazino[4,3-a]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.
Topics & Concepts
ChemistryThioetherMoietyReagentSulfurIndole testCombinatorial chemistryTransformation (genetics)StereochemistryOrganic chemistryBiochemistryGeneFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesSynthesis and Biological Evaluation