Primary Vinyl Ethers as Acetylene Surrogate: A Flexible Tool for Deuterium-Labeled Pyrazole Synthesis

Maria S. Ledovskaya, Vladimir V. Voronin, Mikhail V. Polynski, Andrey N. Lebedev, Valentine P. Ananikov

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

A novel synthetic path to 1,3-disubstituted pyrazoles and their deuterated derivatives was developed. It is based on the reaction of vinyl ethers with hydrazonoyl chlorides in the presence of triethylamine. The reaction mechanism, clarified by the joint experimental and computational study, involves 1,3-dipolar cycloaddition of the in situ generated nitrile imines to vinyl ethers and subsequent cleavage of alcohol from the formed alkoxypyrazoline. The results highlight the possibility of using vinyl ethers as acetylene surrogate and provide a novel access to pyrazoles, 4,5-dideuteropyrazoles and their regioselectively labeled derivatives, 5-deuteropyrazoles.

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
DOIs
StateAccepted/In press - 2020

Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Keywords

  • Cycloaddition
  • Deuterium
  • Deuteropyrazole
  • Isotopic labeling
  • Vinyl ethers

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