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Electrochemical Synthesis of 2,5‐Disubstituted 1,3,4‐Oxadiazoles from α‐Keto Acids and Acylhydrazines Under Mild Conditions
Author(s) -
Lu Fangling,
Gong Fengping,
Li Liangsen,
Zhang Kan,
Li Zhen,
Zhang Xinwei,
Yin Ying,
Wang Ying,
Gao Ziwei,
Zhang Heng,
Lei Aiwen
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000311
Subject(s) - chemistry , yield (engineering) , electrochemistry , combinatorial chemistry , catalysis , intermolecular force , base (topology) , substrate (aquarium) , molecule , transformation (genetics) , organic chemistry , electrode , mathematical analysis , biochemistry , materials science , oceanography , mathematics , metallurgy , gene , geology
1,3,4‐Oxadiazoles are a kind of useful heterocycles which can be frequently found in materials and bioactive molecules. In this study, intermolecular electrochemical cyclization between α‐keto acids and acylhydrazines has been developed for the synthesis of 2,5‐disubstituted 1,3,4‐oxadiazoles with the yield up to 91 %. This transformation can be run under mild reaction conditions in the absence of external oxidant, base and transition metal catalyst. Both symmetrical and unsymmetrical 2,5‐disubstituted 1,3,4‐oxadiazoles could be prepared according to the careful choice of the substrate combination. Gram scale synthesis also illustrates the potential application of this protocol in large preparation.