水中基于异氰化物的多组分反应:合成杂环化合物的先进绿色工具

IF 7.1 2区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Topics in Current Chemistry Pub Date : 2022-09-22 DOI:10.1007/s41061-022-00403-8
Tahereh Nasiriani, Siamak Javanbakht, Mohammad Taghi Nazeri, Hassan Farhid, Vida Khodkari, Ahmad Shaabani
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引用次数: 10

摘要

对化学家来说,利用绿色方法加速反应速率是一个有趣的研究领域。在这方面,水作为一种“绿色溶剂”在加速某些有机转化方面起着至关重要的作用,与传统有机溶剂相比,它显示出独特的选择性和反应性。特别是,多组分反应(mcr)作为可持续的工具,由于疏水效应的突出作用,导致水和水介质中小分子文库的快速生成。mcr作为一种面向多样性的合成方法,具有操作简单、原子、锅、步合成经济、机械美观等优点。在各类多组分反应中,基于异氰化物的多组分反应(i - mcr)作为一种可持续的多用途反应,由于异氰化物作为一种特殊的活性反应物的特性,在各种杂环的合成中,特别是在药物设计中受到了相当大的关注。在水中进行的i - mcr温和、环保、易于控制,并且减少了作业、净化和提取步骤,非常符合“绿色”化学的优势。在水和水介质中进行这些强大的有机转化伴随着负激活体积的加速,这源于将几个反应物连接在一起产生单一产物。应该指出的是,MCR策略与水相反应的结合对有机转化中可持续合成技术的发展越来越有兴趣。然而,关于在水和含水介质中构建杂环的生态友好型i - mcr的最新进展的独家报道尤其缺乏。本文重点介绍了各种i - mcr在水和水介质中作为高效构建重要杂环支架的良性方法的进展,并在2000-2021年期间对该主题进行了批判性讨论。我们希望这个主题的集合将引起有机和药物化学家的兴趣和有益的,并将在这个迷人的领域激发更多的反应发展。图形抽象
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Isocyanide-Based Multicomponent Reactions in Water: Advanced Green Tools for the Synthesis of Heterocyclic Compounds

Reaction rate acceleration using green methods is an intriguing area of research for chemists. In this regard, water as a “green solvent” plays a crucial role in the acceleration of some organic transformations and reveals exclusive selectivity and reactivity in comparison with conventional organic solvents. In particular, multicomponent reactions (MCRs) as sustainable tools lead to the rapid generation of small-molecule libraries in water and aqueous media due to the prominent role of the hydrophobic effect. MCRs, as diversity-oriented synthesis (DOS) methods, have great efficiency with simple operations, atom, pot, and step economy synthesis, and mechanistic beauty. Among diverse classes of MCRs, isocyanide-based multicomponent reactions (I-MCRs), as sustainable and versatile reactions, have gained considerable attention in the synthesis of diverse heterocycle rings, especially in drug design because of the peculiar nature of isocyanide as a particular active reactant. I-MCRs that are performed in water are mild, environmentally friendly, and easily controlled, and have a reduced number of workup, purification, and extraction steps, which fit well with the advantages of “green” chemistry. Performing these powerful organic transformations in water and aqueous media is accompanied by acceleration owing to negative activation volumes, which originate from connecting several reactants together to generate a single product. It should be noted that the combination of MCR strategy and aqueous phase reaction is of growing interest for the development of sustainable synthetic techniques in organic conversions. However, an exclusive account focusing on the recent progress in eco-friendly I-MCRs for the construction of heterocycles in water and aqueous media is particularly lacking. This review highlights the progress of various kinds of I-MCRs in water and aqueous media as benign methods for the efficient construction of vital heterocyclic scaffolds, with a critical discussion of the subject in the period 2000–2021. We hope that this themed collection will be of interest and beneficial for organic and pharmaceutical chemists and will inspire more reaction development in this fascinating field.

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来源期刊
Topics in Current Chemistry
Topics in Current Chemistry Chemistry-General Chemistry
CiteScore
13.70
自引率
1.20%
发文量
48
期刊介绍: Topics in Current Chemistry is a journal that presents critical reviews of present and future trends in modern chemical research. It covers all areas of chemical science, including interactions with related disciplines like biology, medicine, physics, and materials science. The articles in this journal are organized into thematic collections, offering a comprehensive perspective on emerging research to non-specialist readers in academia or industry. Each review article focuses on one aspect of the topic and provides a critical survey, placing it in the context of the collection. Selected examples highlight significant developments from the past 5 to 10 years. Instead of providing an exhaustive summary or extensive data, the articles concentrate on methodological thinking. This approach allows non-specialist readers to understand the information fully and presents the potential prospects for future developments.
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