Cascade Reaction of In Situ Generated N -Heteroiminophosphoranes with α,β-Unsaturated Compounds: A Direct Entry to Diverse Pyrazoles Bearing Oxindole Units
Abstract
An efficient method for the in situ generation of N -heteroiminophosphoranes through the electrophilic addition of the terminal N -atom of oxindole diazocompounds to triphenylphosphine has been developed. The subsequent Wittig/6π 1,5-electrocyclization/1,3-H shift cascade reaction of N -heteroiminophosphoranes with α,β-unsaturated aldehydes, ketoesters, and ketones proceeded smoothly in one pot. A series of functionalized pyrazoles bearing an oxindole unit and atropisomeric biarylpyrazoles have been afforded by this tool with good yields and high functional group tolerance under mild conditions.
Fields of Study & Subjects
Phosphorus compounds and reactions
Cyclopropane Reaction Mechanisms
Organophosphorus compounds synthesis
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Volume
- 91
- Issue
- 10
- Pages
- 3900–3905
- Publication date
- 26 February 2026
- Language
- EN