Regioselective 1,3-dipolar cycloaddition of nitriles with nitrile imines generated from tetrazoles

Tomoya Miura, Kohei Hagiwara, Takayuki Nakamuro, Yuuya Nagata, Naoki Oku, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

A synthesis of 3,5-disubstituted-1,2,4-triazoles from nitriles and 5-aryltetrazoles is reported. When 5-aryltetrazoles are triflylated in the presence of nitriles, the resulting 5-aryl-2-triflyltetrazoles thermally generate N-triflyl-nitrile imines through a sequence of ring-chain tautomerization and denitrogenation. The N-triflyl-nitrile imines immediately undergo 1,3-dipolar cycloaddition with nitriles in a regioselective manner, forming the corresponding 1,2,4-triazoles.

Original languageEnglish
Pages (from-to)131-135
Number of pages5
JournalChemistry Letters
Volume50
Issue number1
DOIs
Publication statusPublished - Jan 2021
Externally publishedYes

Keywords

  • Cycloaddition
  • Nitrile imines
  • Tetrazoles

ASJC Scopus subject areas

  • Chemistry(all)

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