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N-碘对甲苯磺酰胺钾（TsNIK，碘胺-T）：一种将腙氧化为重氮化合物的新型试剂。

Potassium N-iodo p-toluenesulfonamide (TsNIK, Iodamine-T): a new reagent for the oxidation of hydrazones to diazo compounds.

作者信息

Nicolle Simon M, Moody Christopher J

机构信息

School of Chemistry, University of Nottingham, Nottingham NG7 2RD (UK), Fax: (+44) 115-951-3564.

出版信息

Chemistry. 2014 Apr 7;20(15):4420-5. doi: 10.1002/chem.201304656. Epub 2014 Mar 11.

DOI:10.1002/chem.201304656
PMID:24615944
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4164276/
Abstract

A new reagent for the oxidation of hydrazones to diazo compounds is described. N-Iodo p-toluenesulfonamide (TsNIK, iodamine-T) allows the preparation of α-diazoesters, α-diazoamides, α-diazoketones and α-diazophosphonates in good yield and in high purity after a simple extractive work-up. α-Diazoesters were also obtained in high yield from the corresponding ketones through a one-pot process of hydrazone formation/oxidation.

摘要

本文描述了一种用于将腙氧化为重氮化合物的新型试剂。N-碘对甲苯磺酰胺（TsNIK，碘胺-T）可通过简单的萃取后处理，以良好的产率和高纯度制备α-重氮酯、α-重氮酰胺、α-重氮酮和α-重氮膦酸酯。通过腙形成/氧化的一锅法，也可从相应的酮中高产率地获得α-重氮酯。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cf8/4164276/9be65f87f84d/chem0020-4420-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cf8/4164276/c18976267855/chem0020-4420-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cf8/4164276/9be65f87f84d/chem0020-4420-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cf8/4164276/c18976267855/chem0020-4420-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cf8/4164276/9be65f87f84d/chem0020-4420-f2.jpg

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本文引用的文献

1
Catalytic X-H insertion reactions based on carbenoids.基于碳烯的催化 X-H 插入反应。
Chem Soc Rev. 2013 Jun 21;42(12):4918-31. doi: 10.1039/c3cs35496b.
2
Rapid access to α-alkoxy and α-amino acid derivatives through safe continuous-flow generation of diazoesters.通过安全的重氮酯连续流生成快速获取α-烷氧基和α-氨基酸衍生物。
Chemistry. 2011 Aug 22;17(35):9586-9. doi: 10.1002/chem.201101590. Epub 2011 Jul 27.
3
Diazo preparation via dehydrogenation of hydrazones with "activated" DMSO.通过用“活化的”二甲基亚砜使腙脱氢进行重氮制备。
五至七元环α-重氮单羰基化合物的制备及合成应用。
Molecules. 2022 Mar 21;27(6):2030. doi: 10.3390/molecules27062030.
4
Asymmetric synthesis of pharmaceutically relevant 1-aryl-2-heteroaryl- and 1,2-diheteroarylcyclopropane-1-carboxylates.药学相关的1-芳基-2-杂芳基和1,2-二杂芳基环丙烷-1-羧酸酯的不对称合成。
Chem Sci. 2021 Jul 27;12(33):11181-11190. doi: 10.1039/d1sc02474d. eCollection 2021 Aug 25.
5
Experimental and Theoretical Mechanistic Study on the Thermal Decomposition of 3,3-diphenyl-4-(trichloromethyl)-5-nitropyrazoline.3,3-二苯基-4-(三氯甲基)-5-硝基吡唑啉的热分解的实验与理论机理研究。
Molecules. 2021 Mar 4;26(5):1364. doi: 10.3390/molecules26051364.
6
A Conjugate Addition Approach to Diazo-Containing Scaffolds with β Quaternary Centers.一种构建含β-季碳中心重氮骨架的共轭加成方法。
Angew Chem Int Ed Engl. 2020 Jul 27;59(31):12827-12831. doi: 10.1002/anie.202004557. Epub 2020 May 25.
7
Thermal Stability and Explosive Hazard Assessment of Diazo Compounds and Diazo Transfer Reagents.重氮化合物和重氮转移试剂的热稳定性及爆炸危险性评估
Org Process Res Dev. 2020 Jan 17;24(1):67-84. doi: 10.1021/acs.oprd.9b00422. Epub 2019 Nov 28.
8
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9
Non-stabilized diazoalkane synthesis the oxidation of free hydrazones by iodosylbenzene and application in MIRC cyclopropanation.非稳定重氮烷的合成——碘苯对游离腙的氧化及其在MIRC环丙烷化反应中的应用
Chem Sci. 2019 Feb 19;10(13):3802-3806. doi: 10.1039/c8sc05558k. eCollection 2019 Apr 7.
Org Lett. 2007 Apr 26;9(9):1789-92. doi: 10.1021/ol070515w. Epub 2007 Apr 5.
4
Observations on the reaction of hydrazones with iodine: interception of the diazo intermediates.腙与碘反应的观察：重氮中间体的截留
Chem Commun (Camb). 2006 May 7(17):1831-2. doi: 10.1039/b602580c. Epub 2006 Mar 30.
5
A general procedure for the esterification of carboxylic acids with diazoalkanes generated in situ by the oxidation of N-tert-butyldimethylsilylhydrazones with (difluoroiodo)benzene.一种通过用（二氟碘）苯氧化N-叔丁基二甲基硅基腙原位生成重氮烷烃来实现羧酸酯化的通用方法。
J Am Chem Soc. 2004 Oct 6;126(39):12222-3. doi: 10.1021/ja0459779.
6
o-Iodoxybenzoic acid (IBX) as a viable reagent in the manipulation of nitrogen- and sulfur-containing substrates: scope, generality, and mechanism of IBX-mediated amine oxidations and dithiane deprotections.邻碘苯甲酸（IBX）作为一种用于含氮和含硫底物处理的可行试剂：IBX介导的胺氧化和二硫烷脱保护反应的范围、普遍性及机理
J Am Chem Soc. 2004 Apr 28;126(16):5192-201. doi: 10.1021/ja0400382.
7
Cascade Processes of Metallo Carbenoids.金属卡宾的级联反应过程。
Chem Rev. 1996 Feb 1;96(1):223-270. doi: 10.1021/cr950022h.
8
Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates.杂芳基重氮乙酸酯的催化不对称环丙烷化反应
J Org Chem. 2001 Oct 5;66(20):6595-603. doi: 10.1021/jo015617t.
9
Amino-acids and peptides. Part I. Esterification of the carboxy-group of penicillins and cephalosporins by hydrazone oxidation.氨基酸与肽。第一部分。通过腙氧化对青霉素和头孢菌素羧基的酯化反应。
J Chem Soc Perkin 1. 1975(20):2019-22.