DOI

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
Pages (from-to)4571-4580
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number29
DOIs
StatePublished - 9 Aug 2020

    Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

    Research areas

  • Cycloaddition, Deuterium, Deuteropyrazole, Isotopic labeling, Vinyl ethers, AUXILIARY BASIS-SETS, HYDROXYLAMINE, ONE-POT SYNTHESIS, MOLECULAR-ORBITAL METHODS, THERMOCHEMISTRY, DRUG DISCOVERY, CALCIUM CARBIDE, NUCLEOPHILIC-ADDITION, REGIOSELECTIVITY, 1,3-DIPOLAR CYCLOADDITION

ID: 61006485