Regioselective synthesis of either 1H- or 2H-1,2,3-triazoles via Michael addition to α,β-unsaturated ketones

Sen Wai Kwok, Jason E. Hein, Valery V. Fokin, K. Barry Sharpless

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The Michael reaction of NH-1,2,3-triazole (1) with α,β-unsaturated ketones was studied. 1H-1,2,3-triazolyl-ketones were selectively generated when 1 was combined neat with a variety of enones. The use of aprotic solvents with catalytic base gave the corresponding 2H-regioisomers. Together, these two protocols provide direct access to either the N1- or N2-substituted 1,3-triazolyl ketone regioisomers.

Original languageEnglish
Pages (from-to)1141-1154
Number of pages14
JournalHeterocycles
Volume76
Issue number2
DOIs
Publication statusPublished - 1 Nov 2008
Externally publishedYes

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Triazoles
Ketones

Keywords

  • Click Chemistry
  • Michael Reaction
  • N1 - to N2- Isomerization
  • NH-1,2,3-triazole
  • Solvent-Free Reaction

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Regioselective synthesis of either 1H- or 2H-1,2,3-triazoles via Michael addition to α,β-unsaturated ketones. / Kwok, Sen Wai; Hein, Jason E.; Fokin, Valery V.; Sharpless, K. Barry.

In: Heterocycles, Vol. 76, No. 2, 01.11.2008, p. 1141-1154.

Research output: Contribution to journalArticle

Kwok, Sen Wai ; Hein, Jason E. ; Fokin, Valery V. ; Sharpless, K. Barry. / Regioselective synthesis of either 1H- or 2H-1,2,3-triazoles via Michael addition to α,β-unsaturated ketones. In: Heterocycles. 2008 ; Vol. 76, No. 2. pp. 1141-1154.
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