Stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via a Beckmann rearrangement facilitated by diphenyl phosphorazidate

TETRAHEDRON LETTERS

卷:60

Article

Ishihara, Kotaro¹  Shioiri, Takayuki¹  Matsugi, Masato¹ 

[1] Meijo Univ, Fac Agr, Tempa Ku, 1-501 Shiogamaguchi, Nagoya, Aichi 4688502, Japan

关键词: Ketoxime;    Beckmann rearrangement;    Diphenyl phosphorazidate;    Tetrazole;   

DOI  :  10.1016/j.tetlet.2019.04.014

来源: Elsevier

【 摘 要 】

A novel method for the stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via the Beckmann rearrangement was developed using diphenyl phosphorazidate (DPPA) as both the oxime activator and azide source. Various ketoximes were transformed into the corresponding 1,5-disubstituted tetrazoles with exclusive trans-group migration and no E-Z isomerization of the ketoxime. This method enables the preparation of 1,5-disubstituted tetrazoles without using toxic or explosive azidation reagents. (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

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