One-pot Synthesis of Oxindoles through C-H Alkylation and Intramolecular Cyclization of Azobenzenes with Internal Olefins

被引：36

作者：

Han, Sang Hoon ^{[1
]}

Mishra, Neeraj Kumar ^{[1
]}

Jo, Hyeim ^{[1
]}

Oh, Yongguk ^{[1
]}

Jeon, Mijin ^{[1
]}

Kim, Saegun ^{[1
]}

Kim, Woo Jung ^{[2
]}

Lee, Jong Suk ^{[2
]}

Kim, Hyung Sik ^{[1
]}

Kim, In Su ^{[1
]}

机构：

[1] Sungkyunkwan Univ, Sch Pharm, Suwon 16419, South Korea

[2] GBSA, Bioctr, Suwon 16229, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 14期

基金：

新加坡国家研究基金会;

关键词：

Azobenzenes; C-H Activation; Internal olefins; Cyclization; Oxindoles; Rhodium; CATALYTIC ASYMMETRIC-SYNTHESIS; BOND FORMATION; DERIVATIVES; FUNCTIONALIZATION; ANNULATION; MALEIMIDES; ACTIVATION; ACCESS; C-3;

D O I：

10.1002/adsc.201700147

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The rhodium(III)-catalyzed site-selective C-H alkylation of azobenzenes and internal olefins, such as maleimides, maleates and fumarates, followed by reductive intramolecular cyclization is described. A cationic rhodium catalyst in the presence of acetic acid additive in dichloroethane solvent was found to be the optimal catalytic system for the construction of ortho-alkylated azobenzenes, which smoothly underwent the intramolecular cyclization leading to the formation of C3-functionalized oxindoles in the presence of zinc powder and acetic acid. The formed oxindole scaffold could be an important asset towards the development of novel bioactive compounds.

引用

页码：2396 / 2401

页数：6

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