Nucleophile-Induced Rearrangement of 2H-Azirine-2-carbonyl Azides to 2-(1H-Tetrazol-1-yl)acetic Acid Derivatives

Autor:	Alexander F. Khlebnikov, Olesya A. Tomashenko, Mikhail S. Novikov, Nikita I. Efimenko, Dar’ya V. Spiridonova
Rok vydání:	2021
Předmět:	chemistry.chemical_classification Azirine Aryl Organic Chemistry Biochemistry Medicinal chemistry Catalysis chemistry.chemical_compound Acetic acid chemistry Nucleophile Hydrazoic acid Phenols Physical and Theoretical Chemistry Alkyl
Zdroj:	Organic Letters. 23:6362-6366
ISSN:	1523-7052 1523-7060
Popis:	2H-Azirine-2-carbonyl azides undergo a rearrangement into derivatives of 2-(1H-tetrazol-1-yl)acetic acid when interacting with O- and S-nucleophiles at room temperature. The reaction is catalyzed by tertiary amines or hydrazoic acid. The reaction with primary alcohols and phenols gives alkyl/aryl 2-(1H-tetrazol-1-yl)acetates. Thiophenols react with 2H-azirine-2-carbonyl azides to afford S-aryl 2-(1H-tetrazol-1-yl)ethanethioates. The mechanism of the nucleophile-induced rearrangement of 2H-azirine-2-carbonyl azides is discussed on the basis of DFT calculations as well as kinetic and 15N labeling experiments.
Databáze:	OpenAIRE
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