Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102, USA.
Org Biomol Chem. 2021 Apr 26;19(15):3274-3286. doi: 10.1039/d1ob00061f.
Azetidines represent one of the most important four-membered heterocycles used in organic synthesis and medicinal chemistry. The reactivity of azetidines is driven by a considerable ring strain, while at the same the ring is significantly more stable than that of related aziridines, which translates into both facile handling and unique reactivity that can be triggered under appropriate reaction conditions. Recently, remarkable advances in the chemistry and reactivity of azetidines have been reported. In this review, we provide an overview of the synthesis, reactivity and application of azetidines that have been published in the last years with a focus on the most recent advances, trends and future directions. The review is organized by the methods of synthesis of azetidines and the reaction type used for functionalization of azetidines. Finally, recent examples of using azetidines as motifs in drug discovery, polymerization and chiral templates are discussed.
氮杂环丁烷是有机合成和药物化学中最重要的四元杂环之一。氮杂环丁烷的反应性受相当大的环张力驱动，而同时其环的稳定性明显高于相关的氮丙啶，这转化为易于处理和独特的反应性，可以在适当的反应条件下触发。最近，氮杂环丁烷的化学和反应性方面取得了显著进展。在这篇综述中，我们概述了近年来发表的关于氮杂环丁烷的合成、反应性和应用的研究，重点介绍了最新的进展、趋势和未来方向。综述按照氮杂环丁烷的合成方法和用于氮杂环丁烷官能化的反应类型进行组织。最后，讨论了将氮杂环丁烷作为药物发现、聚合和手性模板中的主题的最新实例。
