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炔烃作为某些有机人名反应中的优势合成子。

Alkynes as Privileged Synthons in Selected Organic Name Reactions.

作者信息

Heravi Majid M, Dehghani Mahzad, Zadsirjan Vahideh, Ghanbarian Manijheh

机构信息

Department of Chemistry, School of Science, Alzahra University, Vanak, Tehran, Iran.

出版信息

Curr Org Synth. 2019;16(2):205-243. doi: 10.2174/1570179416666190126100744.

DOI:10.2174/1570179416666190126100744
PMID:31975673
Abstract

BACKGROUND

Alkynes are actually basic chemicals, serving as privileged synthons for planning new organic reactions for assemblage of a reactive motif, which easily undergoes a further desirable transformation. Name reactions, in organic chemistry are referred to those reactions which are well-recognized and reached to such status for being called as their explorers, discoverers or developers. Alkynes have been used in various name reactions. In this review, we try to underscore the applications of alkynes as privileged synthons in prevalent name reactions such as Huisgen 1,3-dipolar cycloaddtion via Click reaction, Sonogashira reaction, and Hetero Diels-Alder reaction.

OBJECTIVE

In this review, we try to underscore the applications of alkynes as privileged synthons in the formation of heterocycles, focused on the selected reactions of alkynes as a synthon or impending utilization in synthetic organic chemistry, which have reached such high status for being included in the list of name reactions in organic chemistry.

CONCLUSION

Alkynes (including acetylene) are an unsaturated hydrocarbon bearing one or more triple C-C bond. Remarkably, alkynes and their derivatives are frequently being used as molecular scaffolds for planning new organic reactions and installing reactive functional group for further reaction. It is worth mentioning that in general, the terminal alkynes are more useful and more frequently being used in the art of organic synthesis. Remarkably, alkynes have found different applications in pharmacology, nanotechnology, as well as being known as appropriate starting precursors for the total synthesis of natural products and biologically active complex compounds. They are predominantly applied in various name reactions such as Sonogashira, Glaser reaction, Friedel-crafts reaction, Castro-Stephens coupling, Huisgen 1.3-dipolar cycloaddtion reaction via Click reaction, Sonogashira reaction, hetero-Diels-Alder reaction. In this review, we tried to impress the readers by presenting selected name reactions, which use the alkynes as either stating materials or precursors. We disclosed the applications of alkynes as a privileged synthons in several popular reactions, which reached to such high status being classified as name reactions. They are thriving and well known and established name reactions in organic chemistry such as Regioselective, 1,3-dipolar Huisgen cycloaddtion reaction via Click reaction, Sonogashira reaction and Diels-Alder reaction.

摘要

背景

炔烃实际上是基础化学品,作为构建反应性基序的新型有机反应设计中的优势合成子,能轻松进行进一步的理想转化。有机化学中的“人名反应”是指那些得到广泛认可,并因其探索者、发现者或开发者而获得这一地位的反应。炔烃已被用于各种人名反应。在本综述中,我们试图强调炔烃作为优势合成子在常见人名反应中的应用,如通过点击反应进行的惠斯根1,3 -偶极环加成反应、Sonogashira反应和杂环狄尔斯 - 阿尔德反应。

目的

在本综述中,我们试图强调炔烃作为优势合成子在杂环形成中的应用,重点关注炔烃作为合成子的选定反应或在有机合成化学中的即将应用,这些反应已达到被列入有机化学人名反应列表的高度地位。

结论

炔烃(包括乙炔)是含有一个或多个碳 - 碳三键的不饱和烃。值得注意的是,炔烃及其衍生物经常被用作设计新型有机反应和引入反应性功能基团以进行进一步反应的分子骨架。值得一提的是,一般来说,末端炔烃在有机合成领域更有用且更常被使用。值得注意的是,炔烃在药理学、纳米技术中已发现不同应用,并且是天然产物和生物活性复杂化合物全合成的合适起始前体。它们主要应用于各种人名反应,如Sonogashira反应、格拉泽反应、傅克反应、卡斯特罗 - 斯蒂芬斯偶联反应、通过点击反应进行的惠斯根1,3 -偶极环加成反应、Sonogashira反应、杂环狄尔斯 - 阿尔德反应。在本综述中,我们试图通过介绍使用炔烃作为起始原料或前体的选定人名反应给读者留下深刻印象。我们揭示了炔烃作为优势合成子在几种常见反应中的应用,这些反应已达到被归类为人名反应的高度地位。它们是有机化学中蓬勃发展、广为人知且已确立的人名反应,如通过点击反应进行的区域选择性1,3 -偶极惠斯根环加成反应、Sonogashira反应和狄尔斯 - 阿尔德反应。

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