Stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via a Beckmann rearrangement facilitated by diphenyl phosphorazidate |
| |
| Institution: | 1. Saint Petersburg State Institute of Technology (Technical University), Saint Petersburg, Russia;4. Saint Petersburg State University, Saint Petersburg, Russia |
| |
| Abstract: | 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. |
| |
| Keywords: | Ketoxime Beckmann rearrangement Diphenyl phosphorazidate Tetrazole |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
