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- Title
Primary Vinyl Ethers as Acetylene Surrogate: A Flexible Tool for Deuterium‐Labeled Pyrazole Synthesis.
- Authors
Ledovskaya, Maria S.; Voronin, Vladimir V.; Polynski, Mikhail V.; Lebedev, Andrey N.; Ananikov, Valentine P.
- 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.
- Subjects
VINYL ethers; NITRILIMINES; PYRAZOLES; ACETYLENE; PYRAZOLE derivatives
- Publication
European Journal of Organic Chemistry, 2020, Vol 2020, Issue 29, p4571
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202000674