Selected Electrosynthesis of 3‑Aminopyrazoles from α,β-Alkynic Hydrazones and Secondary Amines

An available and simple electromediated cyclization method for 3-amino-substituted pyrazoles by using α,β-alkynic hydrazone and secondary amine is described. The strategy utilizes KI as an electrolyte in an undivided cell with a constant current, generating the desired products in moderate-to-good y...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2024-05, Vol.89 (9), p.6520-6526
Hauptverfasser: Tang, Dong, Zhang, Wei, Ji, Jingwen, Jiang, Rui, Wan, Yaya, Ma, Wei, Zhou, Pengjuan
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:An available and simple electromediated cyclization method for 3-amino-substituted pyrazoles by using α,β-alkynic hydrazone and secondary amine is described. The strategy utilizes KI as an electrolyte in an undivided cell with a constant current, generating the desired products in moderate-to-good yield. The method features selective amination at the 3-position of the pyrazole skeleton. The results indicate that α,β-alkynic hydrazones functionalized with aromatic groups and secondary amines functionalized with electron-rich groups were better tolerated in this transformation.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02995