Premium
A Mild Method for Access to α‐Substituted Dithiomalonates through C‐Thiocarbonylation of Thioester: Synthesis of Mesoionic Insecticides
Author(s) -
Yang Xinyue,
Ma Yanrong,
Di Huiming,
Wang Xiaochen,
Jin Hui,
Ryu Do Hyun,
Zhang Lixin
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100369
Subject(s) - mesoionic , chemistry , thioester , imidazole , keto–enol tautomerism , combinatorial chemistry , acylation , organic chemistry , stereochemistry , tautomer , catalysis , enzyme
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.