Highly Efficient InBr3 Catalyzed Michael Addition of Indoles to α,β-Unsaturated Esters

被引：5

作者：

Liu Ping ^{[1
]}

Chen Wei ^{[1
]}

Ren Kai ^{[1
]}

Wang Lei ^{[1
,2
]}

机构：

[1] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2010年 / 28卷 / 12期

基金：

中国国家自然科学基金;

关键词：

Michael addition; indole; alpha; beta-unsaturated ester; Lewis acid; InBr3; CONJUGATE ADDITION; INDIUM TRIBROMIDE; WATER; ACID; ALKALOIDS; TRIFLUOROMETHANESULFONATES; HAPALINDOLES; ALKYLATION; KETONES; ENONES;

D O I：

10.1002/cjoc.201190011

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly efficient synthetic strategy toward Michael addition of indoles to alpha,beta-unsaturated esters has been developed using Lewis acid InBr3 as catalyst. The reactions generated 3-substituted indoles in high yields with excellent regio-selectivity in the presence of catalytic amount of InBr3 under mild reaction conditions. The method is simple, efficient and practical.

引用

页码：2399 / 2403

页数：5

共 50 条

[21] Amine-Squaramide Catalyzed Asymmetric Michael Addition of Cyclic Diketones and β,γ-unsaturated α-keto Esters
Liu, Zhi-Jing
Ma, Zhi-Wei
Chen, Xiao-Pei
Wang, Chuan-Chuan
Liu, Jun-Tao
Tao, Jing-Chao
LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (11) : 1042 - 1046
[22] Highly effective and regioselective Michael addition of indoles to α,β-unsaturated ketones promoted by pentafluorophenylammonium triflate
Khaksar, Samad
Vahdat, Seyed Mohammad
Rezaee, Fatemeh
COMPTES RENDUS CHIMIE, 2013, 16 (02) : 144 - 147
[23] ZrCl4 catalyzed highly selective and efficient Michael addition of heterocyclic enamines with α,β-unsaturated olefins
Kumar, Vijay
Kaur, Sukhdeep
Kumar, Subodh
TETRAHEDRON LETTERS, 2006, 47 (39) : 7001 - 7005
[24] A practical and efficient intramolecular Michael addition of ureas to α,β-unsaturated esters
Xin, ZL
Pei, ZH
von Geldem, T
Jirousek, M
TETRAHEDRON LETTERS, 2000, 41 (08) : 1147 - 1150
[25] Organocatalytic Asymmetric Michael Addition of 4-Hydroxycoumarin to β,γ-Unsaturated α-Keto Esters
Suh, Chang Won
Han, Tae Hyun
Kim, Dae Young
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (06): : 1623 - 1624
[26] Indium Triflate Catalyzed Michael Addition of Amines to a,β-Unsaturated Esters and Nitriles: Synthesis of β-Amino Esters and Nitriles
Thirupathaiah, A.
Rao, G. Venkateshwar
ASIAN JOURNAL OF CHEMISTRY, 2009, 21 (01) : 375 - 378
[27] A Green and Efficient Michael Addition of Indoles to α, β-unsaturated Electron-deficient Compounds and Synthesis of Bis-indolylmethanes Catalyzed by Gallium Dodecyl Sulfate [Ga(DS)3] in Water
Jiang, Jing
Cai, Yuan
Tang, Lixin
JOURNAL OF NEW MATERIALS FOR ELECTROCHEMICAL SYSTEMS, 2017, 20 (01) : 31 - 37
[28] Highly enantioselective Michael addition of malononitrile to α,β-unsaturated pyrazolamides catalyzed by a bifunctional thiourea
Zheng, Yuanqin
Yao, Yongqi
Ye, Ling
Shi, Zhichuan
Li, Xuefeng
Zhao, Zhigang
Li, Xinying
TETRAHEDRON, 2016, 72 (07) : 973 - 978
[29] Montmorillonite K10-Catalyzed Michael Addition of Indoles to Nitroolefins Under Solvent-Free Conditions
Chen, Wei-Yi
Li, Xin-Sheng
SYNTHETIC COMMUNICATIONS, 2009, 39 (11) : 2014 - 2021
[30] Recyclable graphite oxide catalyzed Friedel-Crafts addition of indoles to α,β-unsaturated ketones
Kumar, A. Vijay
Rao, K. Rama
TETRAHEDRON LETTERS, 2011, 52 (40) : 5188 - 5191

← 1 2 3 4 5 →