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三光气及其在有机反应中的应用十年综述。

A decade review of triphosgene and its applications in organic reactions.

作者信息

Ganiu Moshood O, Nepal Binod, Van Houten Joshua P, Kartika Rendy

机构信息

Department of Chemistry, 232 Choppin Hall, Louisiana State University, Baton Rouge, LA 70803 United States.

出版信息

Tetrahedron. 2020 Nov 20;76(47). doi: 10.1016/j.tet.2020.131553. Epub 2020 Sep 6.

DOI:10.1016/j.tet.2020.131553
PMID:33883783
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8054975/
Abstract

This review article highlights selected advances in triphosgene-enabled organic synthetic reactions that were reported in the decade of 2010-2019. Triphosgene is a versatile reagent in organic synthesis. It serves as a convenient substitute for the toxic phosgene gas. Despite its first known preparation in the late 19th interestingly began only three decades ago. Despite the relatively short history, triphosgene has been proven to be very useful in facilitating the preparation of a vast scope of value-added compounds, such as organohalides, acid chlorides, isocyanates, carbonyl addition adducts, heterocycles, among others. Furthermore, applications of triphosgene in complex molecules synthesis, polymer synthesis, and other techniques, such as flow chemistry and solid phase synthesis, have also emerged in the literature.

摘要

这篇综述文章重点介绍了2010年至2019年这十年间报道的光气参与的有机合成反应的一些进展。双光气是有机合成中的一种通用试剂。它是有毒光气气体的便捷替代品。尽管它最早是在19世纪末制备的,但有趣的是,其在有机合成中的应用仅仅在三十年前才开始。尽管历史相对较短,但双光气已被证明在促进制备各种增值化合物方面非常有用,例如有机卤化物、酰氯、异氰酸酯、羰基加成加合物、杂环化合物等。此外,双光气在复杂分子合成、聚合物合成以及其他技术(如流动化学和固相合成)中的应用也已出现在文献中。

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本文引用的文献

1
Total synthesis of pyrano[3,2-]indole alkaloid fontanesine B by a double cyclization strategy.通过双环化策略全合成吡喃并[3,2-]吲哚生物碱丰塔纳辛B。
RSC Adv. 2019 Apr 3;9(18):10420-10424. doi: 10.1039/c9ra02321f. eCollection 2019 Mar 28.
2
Synthesis of Oxadiazolones with Hydrazides: The Mechanism and the Sensing Application as Sensitive, Rapid, and Visual Fluorescent Sensors for Phosgene.偕二唑酮类化合物与酰肼的合成:作为对光气具有高灵敏度、快速响应和可视化荧光传感性能的传感应用的机理。
Org Lett. 2019 Dec 6;21(23):9497-9501. doi: 10.1021/acs.orglett.9b03688. Epub 2019 Nov 13.
3
Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols.三光气和4-二甲氨基吡啶作为叔醇化学选择性脱水的温和试剂。
Org Lett. 2019 Jul 19;21(14):5611-5615. doi: 10.1021/acs.orglett.9b01959. Epub 2019 Jun 28.
4
Synthesis and Antiproliferative Activities of Conjugates of Paclitaxel and Camptothecin with a Cyclic Cell-Penetrating Peptide.紫杉醇和喜树碱与环细胞穿透肽的缀合物的合成及抗增殖活性。
Molecules. 2019 Apr 11;24(7):1427. doi: 10.3390/molecules24071427.
5
Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives.由邻氨基苯甲酸酐与乙酰乙酸乙酯环缩合制备喹啉:4-羟基-2-甲基喹啉-3-羧酸乙酯及其衍生物的制备
Beilstein J Org Chem. 2018 Sep 28;14:2529-2536. doi: 10.3762/bjoc.14.229. eCollection 2018.
6
Synthesis, antiproliferative activity and molecular docking of thiocolchicine urethanes.硫代秋水仙碱尿烷的合成、抗增殖活性及分子对接。
Bioorg Chem. 2018 Dec;81:553-566. doi: 10.1016/j.bioorg.2018.09.004. Epub 2018 Sep 12.
7
One-Pot Cascade Heterocyclization of γ- and β-Ketomalononitriles to 2,4-Dichloro-Substituted Pyrano[2,3- d]pyrimidines and Furo[2,3- d]pyrimidines Mediated by Triphosgene and Triphenylphosphine Oxide.三光气和三苯基氧化膦介导的γ-和β-酮基丙二腈一锅法串联杂环化反应合成2,4-二氯取代的吡喃并[2,3-d]嘧啶和呋喃并[2,3-d]嘧啶
J Org Chem. 2018 Jun 15;83(12):6423-6431. doi: 10.1021/acs.joc.8b00669. Epub 2018 May 24.
8
Synthesis of exo-Imidazolidin-2-one Dienes, Their Isomerization, and Selectivity in Diels-Alder Cycloadditions.外消旋亚氨基二酮二烯的合成、异构化及其在 Diels-Alder 环加成反应中的选择性。
J Org Chem. 2018 May 18;83(10):5347-5364. doi: 10.1021/acs.joc.7b02344. Epub 2018 Apr 26.
9
Synthesis of Vicinal Dichlorides via Activation of Aliphatic Terminal Epoxides with Triphosgene and Pyridine.通过三光气和吡啶激活脂肪族末端环氧化物合成顺式二氯化合物。
J Org Chem. 2018 Mar 16;83(6):3367-3377. doi: 10.1021/acs.joc.7b03197. Epub 2018 Mar 1.
10
Chloride-Templated Macrocyclization and Anion-Binding Properties of C-Symmetric Macrocyclic Ureas from Sucrose.氯模板化大环化作用和蔗糖衍生的 C 对称大环脲的阴离子结合特性。
Org Lett. 2017 Sep 1;19(17):4596-4599. doi: 10.1021/acs.orglett.7b02198. Epub 2017 Aug 21.