Synthesis of 3,3-disubstituted oxindoles from anilines nitrosated in situ: a radical-promoted reaction of aromatic amines with N-arylacrylamides

被引：15

作者：

Ni, Zhangqin ^{[1
]}

Wang, Sichang ^{[1
]}

Huang, Xin ^{[1
]}

Wang, Jichao ^{[1
]}

Pan, Yuanjiang ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 31007, Zhejiang, Peoples R China

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 19期

基金：

美国国家科学基金会;

关键词：

Oxindoles; Diazonium salts; Aromatic amine; Arylacrylamide; CATALYTIC ASYMMETRIC-SYNTHESIS; INTRAMOLECULAR HECK REACTION; ACTIVATED ALKENES; ARENEDIAZONIUM IONS; C(SP3)H BOND; PHYSOSTIGMINE; ACRYLAMIDES; ENANTIOMER; ARYLATION; SEQUENCE;

D O I：

10.1016/j.tetlet.2015.03.112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient synthesis of 3,3-disubstituted oxindoles is achieved. The corresponding diazonium salts are generated in situ from aromatic amines before these salts undergo a homolytic bond cleavage to produce the aryl radicals. Various oxindoles are obtained by homolytic aromatic substitution and radical cyclization. This procedure is an alternative method to oxindole synthesis. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：2512 / 2516

页数：5

共 40 条

[1] Palladium-Catalyzed Tandem Diperoxidation/C-H Activation Resulting in Diperoxy-oxindole in Air [J].

An, Guanghui ;

Zhou, Wei ;

Zhang, Guangqian ;

Sun, Hao ;

Han, Jianlin ;

Pan, Yi .

ORGANIC LETTERS, 2010, 12 (20) :4482-4485

[2] Synthesis of 2-oxindole derivatives via the intramolecular Heck reaction on solid support [J].

Arumugam, V ;

Routledge, A ;

Abell, C ;

Balasubramanian, S .

TETRAHEDRON LETTERS, 1997, 38 (36) :6473-6476

[3] CATALYTIC ASYMMETRIC-SYNTHESIS OF EITHER ENANTIOMER OF PHYSOSTIGMINE - FORMATION OF QUATERNARY CARBON CENTERS WITH HIGH ENANTIOSELECTION BY INTRAMOLECULAR HECK REACTIONS OF (Z)-2-BUTENANILIDES [J].

ASHIMORI, A ;

MATSUURA, T ;

OVERMAN, LE ;

POON, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :6949-6951

[4] REACTIONS OF PRIMARY ALIPHATIC AMINES WITH NITROUS ACID [J].

COLLINS, CJ .

ACCOUNTS OF CHEMICAL RESEARCH, 1971, 4 (09) :315-&

[5] Catalytic asymmetric synthesis of quaternary carbons bearing two aryl substituents. Enantioselective synthesis of 3-alkyl-3-aryl oxindoles by catalytic asymmetric intramolecular Heck reactions [J].

Dounay, AB ;

Hatanaka, K ;

Kodanko, JJ ;

Oestreich, M ;

Overman, LE ;

Pfeifer, LA ;

Weiss, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6261-6271

[6] The asymmetric intramolecular Heck reaction in natural product total synthesis [J].

Dounay, AB ;

Overman, LE .

CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963

[7] Synthesis of 3,3-Disubstituted Oxindoles by Visible-Light-Mediated Radical Reactions of Aryl Diazonium Salts with N-Arylacrylamides [J].

Fu, Weijun ;

Xu, Fengjuan ;

Fu, Yuqin ;

Zhu, Mei ;

Yu, Jiaqi ;

Xu, Chen ;

Zou, Dapeng .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (23) :12202-12206

[8] RADICAL REACTIONS OF ARENEDIAZONIUM IONS - AN EASY ENTRY INTO THE CHEMISTRY OF THE ARYL RADICAL [J].

GALLI, C .

CHEMICAL REVIEWS, 1988, 88 (05) :765-792

[9] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents [J].

Galliford, Chris V. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8748-8758

[10] Palladium-catalyzed domino Heck/cyanation: synthesis of 3-cyanomethyloxindoles and their conversion to spirooxoindoles [J].

Jaegli, Stephanie ;

Vors, Jean-Pierre ;

Neuville, Luc ;

Zhu, Jieping .

TETRAHEDRON, 2010, 66 (46) :8911-8921

← 1 2 3 4 →