Electrooxidative synthesis of 1,2,3-triazolone 1-amines

Electrooxidative synthesis of 1,2,3-triazolone 1-amines Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2025, Volume: 23, Pages: 4971-4976 Pages count : 6 DOI: 10.1039/d5ob00481k

Authors

Titenkova Kseniia ^1,2 , Chaplygin Daniil A. ² , Fershtat Leonid L. ²

Affiliations

1	Department of Chemistry, Moscow State University, 119991 Leninskie Gory 1-3, Moscow, Russia
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky Prosp., 47, Moscow, Russia

A new method for the synthesis of newly reported heterocycles, namely 1,2,3-triazolone 1-amines, via electrochemically induced intramolecular N–N bond formation was developed. The process involves electrooxidative cyclization of readily available α-aminocarbonyl hydrazones, occurs under mild conditions and enables the preparation of a diverse series of target compounds, although nitrophenyl-substituted substrates undergo decomposition upon electrolysis. Cyclic voltammetry (CV) measurements were also conducted to determine the reaction mechanism and to explain the observed scope limitations. In addition, thermal behavior studies demonstrated moderate thermal stability of several synthesized 1,2,3-triazolone 1-amines in the range of 110–140 °C. Overall, this study represents a promising contribution to the electroorganic synthesis of neglected nitrogen heterocycles for various biomedical and materials science applications.

Titenkova K. , Chaplygin D.A. , Fershtat L.L.
Electrooxidative synthesis of 1,2,3-triazolone 1-amines
Organic & Biomolecular Chemistry. 2025. V.23. P.4971-4976. DOI: 10.1039/d5ob00481k WOS Scopus OpenAlex

Web of science:	WOS:001478113700001
Scopus:	2-s2.0-105004019894
OpenAlex:	W4409700340

DB	Citing
OpenAlex	4
Web of science	4
Scopus	3