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使异吲哚酮与氨基酸参与多组分一锅法1,3-偶极环加成反应——轻松实现结构多样性

Engaging Isatins and Amino Acids in Multicomponent One-Pot 1,3-Dipolar Cycloaddition Reactions-Easy Access to Structural Diversity.

作者信息

Zhao Hua, Zhao Yufen

机构信息

Institute of Drug Discovery Technology, Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences, Ningbo University, Ningbo 315211, China.

出版信息

Molecules. 2023 Sep 7;28(18):6488. doi: 10.3390/molecules28186488.

Abstract

Multicomponent reactions (MCRs) have undoubtedly emerged as the most indispensable tool for organic chemists worldwide, finding extensive utility in the synthesis of intricate natural products, heterocyclic molecules with significant bioactivity, and pharmaceutical agents. The multicomponent one-pot 1,3-dipolar cycloaddition reactions, which were initially conceptualized by Rolf Huisgen in 1960, find extensive application in contemporary heterocyclic chemistry. In terms of green synthesis, the multicomponent 1,3-dipolar cycloaddition is highly favored owing to its numerous advantages, including high step- and atom-economies, remarkable product diversity, as well as excellent efficiency and diastereoselectivity. Among the numerous pieces of research, the most fascinating reaction involves the utilization of azomethine ylides generated from isatins and amino acids that can be captured by various dipolarophiles. This approach offers a highly efficient and convenient method for constructing spiro-pyrrolidine oxindole scaffolds, which are crucial building blocks in biologically active molecules. Consequently, this review delves deeper into the dipolarophiles utilized in the 1,3-dipolar cycloaddition of isatins and amino acids over the past six years.

摘要

多组分反应(MCRs)无疑已成为全球有机化学家最不可或缺的工具,在复杂天然产物、具有显著生物活性的杂环分子和药物制剂的合成中有着广泛的应用。多组分一锅法1,3 -偶极环加成反应最初由罗尔夫·惠斯根于1960年提出,在当代杂环化学中有着广泛应用。就绿色合成而言,多组分1,3 -偶极环加成因其诸多优点而备受青睐,包括高步骤经济性和原子经济性、显著的产物多样性以及出色的效率和非对映选择性。在众多研究中,最引人入胜的反应涉及利用由异吲哚酮和氨基酸生成的甲亚胺叶立德,其可被各种亲偶极体捕获。这种方法为构建螺环吡咯烷氧化吲哚支架提供了一种高效便捷的方法,而螺环吡咯烷氧化吲哚支架是生物活性分子中的关键结构单元。因此,本综述更深入地探讨了过去六年中异吲哚酮和氨基酸的1,3 -偶极环加成反应中所使用的亲偶极体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/34a6/10536439/68d3a4681fc6/molecules-28-06488-g001.jpg

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