Synthesis of Rare 1,2,3-Triazolium-5-olates by Electrooxidative Cyclization of α-Aminocarbonyl Hydrazones

Synthesis of Rare 1,2,3-Triazolium-5-olates by Electrooxidative Cyclization of α-Aminocarbonyl Hydrazones Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2025, Volume: 27, Number: 17, Pages: 4434–4438 Pages count : DOI: 10.1021/acs.orglett.5c00784

Authors

Titenkova Kseniia ^1,2 , Turpakov Egor A. ^2,3 , Chaplygin Daniil A. ² , Fershtat Leonid L. ^2,3

Affiliations

1	Department of Chemistry, Moscow State University Leninskie Gory 1-3, 119991 Moscow, Russia
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, 119991 Moscow, Russia
3	National Research University Higher School of Economics, Myasnitskaya str., 20, 101000 Moscow, Russia

A new method for the synthesis of rare mesoionic heterocycles, namely, 1,2,3-triazolium-5-olates, via electrochemically induced intramolecular N–N bond formation was realized. The process involves electrooxidative cyclization of the readily available α-aminocarbonyl hydrazones, occurs under mild conditions, and enables the preparation of a diverse series of target mesoionics. Additionally, 1,2,3-triazolium-5-olates demonstrated high thermal stability (up to 275 °C) and feature prominent Stokes shifts (7600–8050 cm–1), which enables their application potential for analytical systems and materials science.

Titenkova K. , Turpakov E.A. , Chaplygin D.A. , Fershtat L.L.
Synthesis of Rare 1,2,3-Triazolium-5-olates by Electrooxidative Cyclization of α-Aminocarbonyl Hydrazones
Organic Letters. 2025. V.27. N17. P.4434–4438. DOI: 10.1021/acs.orglett.5c00784 WOS Scopus OpenAlex

Web of science:	WOS:001473244500001
Scopus:	2-s2.0-105004026849
OpenAlex:	W4409706258

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OpenAlex	3
Web of science	3
Scopus	2