Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles by visible-light-mediated decarboxylation–cyclization of hydrazides and diketones

[Display omitted] •The research was proceeded without using transition-metal under visible-light.•The reaction was proceeded without using extra oxidant.•The protocol tolerates a wide range of functional groups.•A plausible mechanism was proposed. A visible-light-induced synthesis of 2,5-disubstitut...

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Bibliographic Details
Published in:Tetrahedron letters 2018-02, Vol.59 (8), p.767-770
Main Authors: Diao, Pinhui, Ge, Yanqin, zhang, Wenpei, Xu, Chen, Zhang, Nannan, Guo, Cheng
Format: Article
Language:English
Subjects:
1,3,4-Oxadiazoles
Cyclization
Decarboxylation
Mild conditions
Visible light
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Summary:[Display omitted] •The research was proceeded without using transition-metal under visible-light.•The reaction was proceeded without using extra oxidant.•The protocol tolerates a wide range of functional groups.•A plausible mechanism was proposed. A visible-light-induced synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from simple diketones and hydrazides with the assistant of the photocatalyst eosin Y catalyzed decarboxylation and cyclization under mild conditions has been discovered. The reaction tolerates a wide range of functional groups and gives a variety of valuable 1,3,4-oxadiazoles in moderate to good yields. Finally, a plausible reaction mechanism was proposed.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.01.037