Non-Aziridination Approaches to 3-Arylaziridine-2-carboxylic Acid Derivatives and 3-Aryl-(aziridin-2-yl)ketones
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Date
2022-06-01
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Abstract
Highly functionalized aziridines, including compounds with aromatic moieties, are attractive substrates both in synthetic and medical areas of chemistry. There is a broad and interesting set of synthetic methods for reaching these compounds. Aziridination represents the most explored tool, but there are several other more specific, less well-known, but highly promising approaches. Therefore, the current review focuses on recently described or updated ways to obtain 3-arylated aziridines via different non-aziridination-based synthetic methods, reported mainly since 2000. The presented methods belong to two main directions of synthesis, namely, cyclization of open-chain substrates and rearrangement of other heterocycles. Cyclization of open-chain substrates includes the classic Gabriel-Cromwell type cyclization of halogenated substrates with amines, base-promoted cyclization of activated aminoalcohols (or its analogues), and the oxidative cyclization of β-dicarbonyls. Rearrangements of other heterocycles are presented as the Baldwin rearrangement of 4-isoxazolines, the cycloaddition of 1.3-dipoles or dienes to 2H-azirines, and the addition of C-and N-nucleophiles to the double bond of azirines.
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Funding Information: APC was covered by Riga Stradins University, Riga, Latvia. Publisher Copyright: © 2022 by the authors. Licensee MDPI, Basel, Switzerland.
Keywords
4-isoxazolines, aziridines, azirines, Baldwin rearrangement, cyclization, cycloaddition, 1.4 Chemical sciences, 1.6 Biological sciences, 3.1 Basic medicine, 1.1. Scientific article indexed in Web of Science and/or Scopus database, Catalysis, Molecular Biology, Spectroscopy, Computer Science Applications, Physical and Theoretical Chemistry, Organic Chemistry, Inorganic Chemistry
Citation
Strumfs, B, Veļikijs, K, Uljanovs, R, Sinkarevs, S & Strumfa, I 2022, 'Non-Aziridination Approaches to 3-Arylaziridine-2-carboxylic Acid Derivatives and 3-Aryl-(aziridin-2-yl)ketones', International Journal of Molecular Sciences, vol. 23, no. 11, 5919. https://doi.org/10.3390/ijms23115919