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.

Язык оригиналаанглийский
Страницы (с-по)4571-4580
Число страниц10
ЖурналEuropean Journal of Organic Chemistry
Том2020
Номер выпуска29
DOI
СостояниеОпубликовано - 9 авг 2020

    Предметные области Scopus

  • Физическая и теоретическая химия
  • Органическая химия

ID: 61006485