Copper powder-catalyzed chelation-assisted cascade reaction of o-chloroarylacetic acids with amines under solvent-and ligand-free conditions: synthesis of oxindoles

Li Jiang-Sheng; Chen Guo-Qin; Yang Qian; Li Zhi-Wei; Liu Ci-Zhi; Huang Peng-Mian

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Copper powder-catalyzed chelation-assisted cascade reaction of o-chloroarylacetic acids with amines under solvent-and ligand-free conditions: synthesis of oxindoles

机译：在溶剂和配体的条件下，铜粉末催化O-氯亚芳乙酸的螯合辅助级联反应：氧胆固醇的合成

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An efficient method to construct oxindole scaffolds from o-chloroarylacetic acids/esters with amines has been explored. This cascade protocol involves the in situ generation of o-aminoarylacetic acid derivatives by the copper powder catalyzed and weak O-chelation assisted Ullmann amination of unactivated C-Cl bonds under air, and solvent-/ligand-free conditions followed by annulative N-acylation.

机译：已经探讨了从O-氯亚氨酸乙酸/酯与胺的氧吲哚支架构建氧吲哚支架的有效方法。该级联方案涉及通过铜粉末催化和弱O螯合物的原位产生O-氨基酰亚乙酸衍生物，辅助O-C-Cl键在空气下辅助ullmann胺化，以及无溶剂/配体的条件，然后是环氧化的N-酰化。。

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《RSC Advances》 |2017年第71期|共5页
作者
Li Jiang-Sheng; Chen Guo-Qin; Yang Qian; Li Zhi-Wei; Liu Ci-Zhi; Huang Peng-Mian;
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作者单位

Changsha Univ Sci &

Technol Sch Chem &

Biol Engn Hunan Prov Key Lab Mat Protect Elect Power &

Tran Changsha 410114 Hunan Peoples R China;

Changsha Univ Sci &

Technol Sch Chem &

Biol Engn Hunan Prov Key Lab Mat Protect Elect Power &

Tran Changsha 410114 Hunan Peoples R China;

Changsha Univ Sci &

Technol Sch Chem &

Biol Engn Hunan Prov Key Lab Mat Protect Elect Power &

Tran Changsha 410114 Hunan Peoples R China;

Changsha Univ Sci &

Technol Sch Chem &

Biol Engn Hunan Prov Key Lab Mat Protect Elect Power &

Tran Changsha 410114 Hunan Peoples R China;

Changsha Univ Sci &

Technol Sch Chem &

Biol Engn Hunan Prov Key Lab Mat Protect Elect Power &

Tran Changsha 410114 Hunan Peoples R China;

Changsha Univ Sci &

Technol Sch Chem &

Biol Engn Hunan Prov Key Lab Mat Protect Elect Power &

Tran Changsha 410114 Hunan Peoples R China;

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正文语种 eng
中图分类化学;
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1. Copper powder-catalyzed chelation-assisted cascade reaction of o-chloroarylacetic acids with amines under solvent-and ligand-free conditions: synthesis of oxindoles [J] . Li Jiang-Sheng, Chen Guo-Qin, Yang Qian, RSC Advances . 2017,第71期

机译：在溶剂和配体的条件下，铜粉末催化O-氯亚芳乙酸的螯合辅助级联反应：氧胆固醇的合成
2. Ligand-free copper powder-catalyzed and (KOBu)-Bu-t-accelerated expeditious synthesis of substituted benzoxazoles [J] . Ahmed Atiur, Singha Raju, Ray Jayanta K. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2015,第17期

机译：无配体铜粉催化和（KOBu）-Bu-t加速合成取代的苯并恶唑
3. Synthesis of Dichlorocyanomethyl-Functionalized Oxindoles by Cascade Reactions Initiated by Copper(I)-Catalytically Generated Dichlorocyanomethyl Radical [J] . Che Fengrui, Zhong Jiangbin, Yu Linhan, Advanced synthesis & catalysis . 2020,第22期

机译：通过铜（I）引发的级联反应 - 催化产生二氯氰菊酯的梯度反应合成二氯氰酸甲基官能化氧吲哚酮
4. Recoverable Nanoparticle Palladium(O) Catalyzed Sonogashira Reaction Under Ligand, Copper and Amine Free Reaction Conditions [C] . 7th International Symposium on Green Chemistry in China(7th ISGCC'2005) . 2005

机译：在无配体，无铜和无胺的条件下可回收的纳米级钯（O）催化的Sonogashira反应
5. Chapter 1: Part 1: A Unique Approach of Preparing 3,3-Disubstituted Oxindoles from Acyclic Tetrasubstituted Aldehydes: Total Synthesis of (-)-Coerulescine and (-)-Coixspirolactam A, Chapter 1: Part 2: Synthetic Scope of Br?nsted Acid Catalyzed Reactions o [D] . Ali, Md Shahnawaz. 2021

机译：第1章：第1部分：从环碳四取代的醛制备3,3-二取代的氧吲哚的独特方法：全合成（ - ） - Coerularcine和（ - ） - Coxspirolactam A，第1章：第2部分：BR的合成范围：NSTED 酸催化反应o
6. Copper-Catalyzed Three- Five- or Seven-Component Coupling Reactions: The Selective Synthesis of Cyanomethylamines NN-Bis(Cyanomethyl)Amines and NN-Bis(Cyanomethyl)Methylenediamines Based on a Strecker-Type Synthesis [O] . Norio Sakai, Nobuaki Takahashi, Daiki Inoda, 2013

机译：铜催化的三元或五元或七元偶联反应：基于Strecker型合成的氰基甲胺NN-双（氰基甲基）胺和NN-双（氰基甲基）亚甲基二胺的选择性合成
7. Aqueous tert-Butyl Hydroperoxide Mediated Regioselective Ring-Opening Reactions of Spiro-aziridine-epoxy Oxindoles: Synthesis of 3Peroxy-3-substituted Oxindoles and Their Acid-Mediated Rearrangement [O] . -1

机译：叔丁基水溶液水溶液介导的螺二氮杂氨酸 - 环氧氧基氧基溶剂的区域选择性开环反应：合成3聚氧基-3-取代的牛吲哚和其酸介导的重排

Copper powder-catalyzed chelation-assisted cascade reaction of o-chloroarylacetic acids with amines under solvent-and ligand-free conditions: synthesis of oxindoles

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