A Mild Method for Access to α‐Substituted Dithiomalonates through C‐Thiocarbonylation of Thioester: Synthesis of Mesoionic Insecticides
Xinyue Yang, Yanrong Ma, Huiming Di, Xiaochen Wang, Hui Jin, Do Hyun Ryu, Lixin Zhang
Abstract
Abstract An efficient method for targeting a variety of symmetrical and asymmetrical α‐substituted dithiomalonates (DTMs) is described, utilizing 1 H ‐imidazole‐1‐carbothioates as reactive acylating agents and MgBr 2 ⋅OEt 2 /DBU or LiHMDS for soft or hard enolization conditions of thioesters, respectively. The utility of this methodology was demonstrated through the synthesis of the pyridopyrimidine mesoionic insecticides: triflumezopyrim and dicloromezotiaz. magnified image
Topics & Concepts
MesoionicChemistryThioesterImidazoleKeto–enol tautomerismCombinatorial chemistryAcylationOrganic chemistryStereochemistryTautomerCatalysisEnzymeSynthesis and Catalytic ReactionsSulfur-Based Synthesis TechniquesSynthesis of heterocyclic compounds