4.4 Article

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

期刊

TETRAHEDRON LETTERS
卷 60, 期 18, 页码 1295-1298

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2019.04.014

关键词

Ketoxime; Beckmann rearrangement; Diphenyl phosphorazidate; Tetrazole

资金

  1. JSPS [19K07006]
  2. Professor Y. Uozumi's JST-ACCEL program [JPMJAC1401]
  3. Grants-in-Aid for Scientific Research [19K07006] Funding Source: KAKEN

向作者/读者索取更多资源

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.

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