Synthesis of 1-substituted tetrazoles via the acid-catalyzed [3+2] cycloaddition between isocyanides and trimethylsilyl azide

Tetsuo Kin, Shin Kamijo, Yoshinori Yamamoto

Research output: Contribution to journalArticlepeer-review

110 Citations (Scopus)

Abstract

1-Substituted tetrazoles were synthesized via the [3+2] cycloaddition between isocyanides and trimethylsilyl azide in the presence of an acid catalyst and MeOH. Various 1-substituted tetrazoles were obtained in good to high yields. The reaction probably proceeds through the in situ formation of hydrazoic acid, followed by a successive [3+2] cycloaddition with the isocyanide activated by an acid.

Original languageEnglish
Pages (from-to)9435-9437
Number of pages3
JournalTetrahedron Letters
Volume45
Issue number51
DOIs
Publication statusPublished - 2004 Dec 13

Keywords

  • 1-Substituted tetrazole
  • Acid-catalyzed reaction
  • Hydrazoic acid
  • Isocyanide
  • Tetrazole
  • Trimethylsilyl azide
  • [3+2] Cycloaddition

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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