Transition-metal-free multinitrogenation of amides by C-C bond cleavage: a new approach to tetrazoles

A metal-free brand-new one-pot multinitrogenation of amides for the chemo- and regioselective synthesis of 1,5-disubstituted tetrazoles has been developed. By means of electrophilic amide activation, and further C-C bond cleavage and rearrangement, a diverse set of functionalized 1,5-DST derivatives...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018, Vol.54 (79), p.11148-11151
Main Authors: Li, Lian-Hua, Niu, Zhi-Jie, Li, Ying-Xiu, Liang, Yong-Min
Format: Article
Language:English
Subjects:
Amides
Cleavage
Crystallography
Ductile-brittle transition
Fracture mechanics
Tetrazoles
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Summary:A metal-free brand-new one-pot multinitrogenation of amides for the chemo- and regioselective synthesis of 1,5-disubstituted tetrazoles has been developed. By means of electrophilic amide activation, and further C-C bond cleavage and rearrangement, a diverse set of functionalized 1,5-DST derivatives were selectively constructed under mild conditions. As showcased in the mechanisms, the chemoselectivity is easily switched by the selection of the starting materials in the reaction. A metal-free brand-new one-pot multinitrogenation of amides for the chemo-, regioselective synthesis of 1,5-disubstituted tetrazoles has been developed.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc06324a