1. Nucleophile-Induced Rearrangement of 2H-Azirine-2-carbonyl Azides to 2-(1H-Tetrazol-1-yl)acetic Acid Derivatives
- Author
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Alexander F. Khlebnikov, Olesya A. Tomashenko, Mikhail S. Novikov, Nikita I. Efimenko, and Dar’ya V. Spiridonova
- Subjects
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 - Abstract
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.
- Published
- 2021
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