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共同缓解压力:通过环化两个不同的张力环来构建具有生物学意义的杂环骨架。

Relieving the stress together: annulation of two different strained rings towards the formation of biologically significant heterocyclic scaffolds.

作者信息

Ghosh Asit, Dey Raghunath, Banerjee Prabal

机构信息

Department of Chemistry, Indian Institute of Technology Ropar, Nangal Road, Rupnagar, Punjab-140001, India.

出版信息

Chem Commun (Camb). 2021 Jun 1;57(44):5359-5373. doi: 10.1039/d1cc00998b.

DOI:10.1039/d1cc00998b
PMID:33969833
Abstract

Small carbo- and heterocycles have become versatile building blocks owing to their intrinsic ring strain and ease of synthesis. However, the traditional approaches of heterocycle synthesis involved the combination of one strained-carbocycle or heterocycle with one unsaturated molecule. On the contrary, there is an exciting possibility of combining two different strained rings to furnish varieties of heterocycles, where one of the strained rings can act as a valuable alternative to the unsaturated molecule. These strategies are also useful to access multi-functionalized rings. Despite these distinctive synthetic benefits, this chemistry has not drawn considerable attention of the community. In this minireview, we explicitly choose this topic to reveal the unexplored possibilities with these different strained rings. This minireview provides comprehensive details with the mechanistic rationale about the reactivity of these pairs of small rings when they are allowed to react together in the presence of different Lewis acids. Subsequently, it will also open a new avenue for heterocycle synthesis.

摘要

由于其固有的环张力和易于合成的特点,小型碳环和杂环已成为多功能的结构单元。然而,传统的杂环合成方法涉及一个张力碳环或杂环与一个不饱和分子的结合。相反,将两个不同的张力环结合以提供各种杂环是一种令人兴奋的可能性,其中一个张力环可以作为不饱和分子的有价值替代物。这些策略对于获得多官能化环也很有用。尽管有这些独特的合成优势,但这种化学尚未引起该领域的广泛关注。在本综述中,我们特意选择这个主题来揭示这些不同张力环未被探索的可能性。本综述提供了关于这些小环对在不同路易斯酸存在下一起反应时反应性的机理原理的全面细节。随后,它也将为杂环合成开辟一条新途径。

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