Empowering strategies of electrochemical N–N bond forming reactions: direct access to previously neglected 1,2,3-triazole 1-oxides

Empowering strategies of electrochemical N–N bond forming reactions: direct access to previously neglected 1,2,3-triazole 1-oxides Full article

Journal

Green Chemistry
ISSN: 1463-9262 , E-ISSN: 1463-9270

Output data

Year: 2023, Volume: 25, Number: 17, Pages: 6686-6693 Pages count : 8 DOI: 10.1039/d3gc01601c

Authors

Titenkova Kseniia Yu. ^1,2 , Shuvaev Alexander D. ^1,2 , Teslenko Fedor E. ^1,2 , Zhilin Egor S. 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

Electrochemical synthesis has become one of the emerging and powerful tools to create novel state-of-the-art strategies for the assembly of complex organic molecules. However, electrochemically induced N–N bond forming reactions still remain challenging due to the relatively high electronegativity of nitrogen and various side reactions associated with the oxidation of N–H bonds. Herein, we present a novel green electrochemical approach for the selective intramolecular formation of N–N bonds via the oxidation of readily available oximinohydrazones. Hence, previously neglected nitrogen heterocycles, 1,2,3-triazole 1-oxides, were prepared through a sustainable transition-metal- and exogenous oxidant-free strategy with broad generality. Based on the obtained cyclic voltammograms and DFT calculations, a plausible mechanism for the oxidation of oximinohydrazones was proposed. According to differential scanning calorimetry (DSC) data, the prepared 1,2,3-triazole 1-oxides may be classified as thermally stable species (Td: 151–242 °C), which are highly valuable for the further development of functional organic materials. Moreover, 1,2,3-triazole 1-oxides were found to exhibit promising NO release properties under physiological conditions, unveiling broad opportunities for the creation of new pharmaceutical ingredients in an environmentally benign fashion.

Titenkova K.Y. , Shuvaev A.D. , Teslenko F.E. , Zhilin E.S. , Fershtat L.L.
Empowering strategies of electrochemical N–N bond forming reactions: direct access to previously neglected 1,2,3-triazole 1-oxides
Green Chemistry. 2023. V.25. N17. P.6686-6693. DOI: 10.1039/d3gc01601c WOS Scopus OpenAlex

Web of science:	WOS:001040392100001
Scopus:	2-s2.0-85168720087
OpenAlex:	W4385154205

DB	Citing
OpenAlex	23
Scopus	22
Web of science	23