A Mild Method for Access to α‐Substituted Dithiomalonates through C‐Thiocarbonylation of Thioester: Synthesis of Mesoionic Insecticides | Zendy

Yang Xinyue | Zendy; Ma Yanrong | Zendy; Di Huiming | Zendy; Wang Xiaochen | Zendy; Jin Hui | Zendy; Ryu Do Hyun | Zendy; Zhang Lixin | Zendy

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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.

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