Copper-catalyzed synthesis of 5-substituted 1H-tetrazoles via the [3+2] cycloaddition of nitriles and trimethylsilyl azide

Tienan Jin, Fukuzou Kitahara, Shin Kamijo, Yoshinori Yamamoto

Research output: Contribution to journalArticlepeer-review

174 Citations (Scopus)

Abstract

The [3+2] cycloaddition between various nitriles and trimethylsilyl azide proceeds smoothly in the presence of a CuI catalyst in DMF/MeOH, to give the corresponding 5-substituted 1H-tetrazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper azide species, followed by a successive [3+2] cycloaddition with the nitriles.

Original languageEnglish
Pages (from-to)2824-2827
Number of pages4
JournalTetrahedron Letters
Volume49
Issue number17
DOIs
Publication statusPublished - 2008 Apr 21

Keywords

  • 5-Substituted 1H-tetrazole
  • Copper azide
  • Copper catalyst
  • Nitrile
  • Trimethylsilyl azide
  • [3+2] Cycloaddition

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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