Electrochemically Induced Synthesis of Imidazoles from Vinyl Azides and Benzyl Amines

An electrochemically induced synthesis of imidazoles from vinyl azides and benzyl amines was developed. A wide range of imidazoles were obtained, with yields of 30 to 64%. The discovered transformation is a multistep process whose main steps include the generation of electrophilic iodine species, 2...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2022-11, Vol.27 (22), p.7721
Main Authors: Vil', Vera A, Grishin, Sergei S, Terent'ev, Alexander O
Format: Article
Language:English
Subjects:
Amines
Antifungal agents
Azide
Azides - chemistry
Catalysis
Chemical reduction
Cyclization
electrochemistry
Hydrocarbons
Imidazole
imidazoles
Imidazoles - chemistry
Intermediates
Iodine
Organic chemistry
Oxidation
vinyl azides
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description An electrochemically induced synthesis of imidazoles from vinyl azides and benzyl amines was developed. A wide range of imidazoles were obtained, with yields of 30 to 64%. The discovered transformation is a multistep process whose main steps include the generation of electrophilic iodine species, 2 -azirine formation from the vinyl azide, followed by its reactions with benzyl amine and with imine generated from benzyl amine. The cyclization and aromatization of the obtained intermediate lead to the target imidazole. The synthesis proceeds under constant current conditions in an undivided cell. Despite possible cathodic reduction of various unsaturated intermediates with C=N bonds, the efficient electrochemically induced synthesis of imidazoles was carried out.
doi_str_mv 10.3390/molecules27227721
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Despite possible cathodic reduction of various unsaturated intermediates with C=N bonds, the efficient electrochemically induced synthesis of imidazoles was carried out.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules27227721</identifier><identifier>PMID: 36431821</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Amines ; Antifungal agents ; Azide ; Azides - chemistry ; Catalysis ; Chemical reduction ; Cyclization ; electrochemistry ; Hydrocarbons ; Imidazole ; imidazoles ; Imidazoles - chemistry ; Intermediates ; Iodine ; Organic chemistry ; Oxidation ; vinyl azides</subject><ispartof>Molecules (Basel, Switzerland), 2022-11, Vol.27 (22), p.7721</ispartof><rights>COPYRIGHT 2022 MDPI AG</rights><rights>2022 by the authors. Licensee MDPI, Basel, Switzerland. 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subjects Amines
Antifungal agents
Azide
Azides - chemistry
Catalysis
Chemical reduction
Cyclization
electrochemistry
Hydrocarbons
Imidazole
imidazoles
Imidazoles - chemistry
Intermediates
Iodine
Organic chemistry
Oxidation
vinyl azides
title Electrochemically Induced Synthesis of Imidazoles from Vinyl Azides and Benzyl Amines
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