Electrochemical oxidative synthesis of 1,3,4-thiadiazoles from isothiocyanates and hydrazones
Literature Information
Publication Date
2021-03-04
DOI
10.1039/D1QO00168J
Impact Factor
5.281
Authors
Zhongxiao Ma, Xiao Hu, Yanni Li, Deqiang Liang, Ying Dong, Baoling Wang, Weili Li
View Original
Abstract
A 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-catalysed electrochemical synthesis of 2-amino-1,3,4-thiadiazoles from isothiocyanates and hydrazones is presented. This protocol is mild, practical, metal-free and exogenous oxidant-free, and features a broad substrate scope. Extensive mechanistic investigations revealed that the reaction proceeds via a tandem addition/chemoselective C–S coupling sequence, and it is the hydrogenated DDQ that is oxidized at the anode, not the intermediate thiosemicarbazides.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
2-Amino-2-(4-(pyridin-2-YL)phenyl)acetic acid hydrochloride
CAS Number:
1135818-89-1
Molecular Formula:
C13H13ClN2O2
(4aS,10aS)-7-Isopropyl-1,4a-dimethyl-5,8-dioxo-3,4,4a,5,8,9,10,10a-octahydro-2-phenanthrenecarboxylic acid
CAS Number:
142950-86-5
Molecular Formula:
C20H24O4
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