A Practical Synthesis of 5-Substituted 1 H -Tetrazoles from Aldoximes Employing the Azide Anion from Diphenyl Phosphorazidate

Kotaro Ishihara, Mayumi Kawashima, Takatoshi Matsumoto, Takayuki Shioiri, Masato Matsugi

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

5-Substituted 1 H -tetrazoles were effectively synthesized from aldoximes and diphenyl phosphorazidate (DPPA) under reflux conditions in xylenes. Various aldoximes underwent the cycloaddition reaction to afford the corresponding 5-substituted 1 H -tetrazoles in short reaction times and in good yields. Chiral aldoximes derived from amino acids also gave aminotetrazoles with almost no racemization.

Original languageEnglish
Pages (from-to)1293-1300
Number of pages8
JournalSynthesis (Germany)
Volume50
Issue number6
DOIs
Publication statusPublished - 2018 Mar 15

Keywords

  • aldoximes
  • azides
  • cycloaddition
  • diphenyl phosphorazidate
  • tetrazoles

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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