Water-soluble (salicyladimine)2Cu complex as an efficient and renewable catalyst for Michael addition of indoles to nitroolefins in water

被引：4

作者：

Jiang, Haojie ^{[1
]}

Zhang, Jie ^{[1
]}

Xie, Jianwei ^{[1
]}

Liu, Ping ^{[1
]}

Xue, Mei ^{[1
]}

机构：

[1] Shihezi Univ, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Sch Chem & Chem Engn, Shihezi 832003, Xinjiang, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2017年 / 47卷 / 03期

关键词：

Indole; Michael addition; nitroolefin; (salicyladimine)(2)Cu complex; water; FRIEDEL-CRAFTS ALKYLATION; SOLVENT-FREE CONDITIONS; SCHIFF-BASE COMPLEXES; BETA-NITROSTYRENES; HIGHLY EFFICIENT; PYRROLE; NITROALKENES; DERIVATIVES; ALPHA; ACID;

D O I：

10.1080/00397911.2016.1258478

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and environmentally friendly protocol has been demonstrated for water-soluble (salicyladimine)(2)Cu complex-catalyzed Michael addition of indoles to nitroolefins in water at 30 degrees C. A variety of substituted indoles and -nitrostyrenes could be worked well to provide the title products in 81-97% yields. Moreover, the catalyst can be reused directly at least for four times without significantly decreasing activity. [GRAPHICS] .

引用

页码：211 / 216

页数：6

共 27 条

[1] Highly Efficient Aluminum Trichloride Catalyzed Michael Addition of Indoles and Pyrroles to Maleimides [J].

An, Yu-Long ;

Shao, Zhi-Yu ;

Cheng, Jian ;

Zhao, Sheng-Yin .

SYNTHESIS-STUTTGART, 2013, 45 (19) :2719-2726

[2]

[Anonymous], 1996, CHEM INDOLES

[3] Efficient Friedel-Crafts alkylation of indoles and pyrrole with enones and nitroalkene in water [J].

Azizi, Najmedin ;

Arynasab, Fezzeh ;

Saidi, Mohammad R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (23) :4275-4277

[4] A practical indium tribromide catalysed addition of indoles to nitroalkenes in aqueous media [J].

Bandini, M ;

Melchiorre, P ;

Melloni, A ;

Umani-ronchi, A .

SYNTHESIS-STUTTGART, 2002, (08) :1110-1114

[5]

Charles C. C. J., 2012, CHEM-EUR J, V18, P13250

[6] A bench-stable homodinuclear Ni2-chiff base complex for catalytic asymmetric synthesis of α-tetrasubstituted anti-α,β-diamino acid surrogates [J].

Chen, Zhihua ;

Morimoto, Hiroyuki ;

Matsunaga, Shigeki ;

Shibasaki, Masakatsu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (07) :2170-+

[7] The facile and efficient Michael addition of indoles and pyrrole to α, β-unsaturated electron-deficient compounds catalyzed by aluminium dodecyl sulfate trihydrate [Al(DS)3]3H2O in water [J].

Firouzabadi, H ;

Iranpoor, N ;

Nowrouzi, F .

CHEMICAL COMMUNICATIONS, 2005, (06) :789-791

[8] 2-Substituted tryptamines:: Agents with selectivity for 5-HT6 serotonin receptors [J].

Glennon, RA ;

Lee, M ;

Rangisetty, JB ;

Dukat, M ;

Roth, BL ;

Savage, JE ;

McBride, A ;

Rauser, L ;

Hufeisen, S ;

Lee, DKH .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) :1011-1018

[9] Catalyst-free aqueous-mediated conjugative addition of indoles to β-nitrostyrenes [J].

Habib, Pateliya Mujjamil ;

Kavala, Veerababurao ;

Kuo, Chun-Wei ;

Yao, Ching-Fa .

TETRAHEDRON LETTERS, 2008, 49 (49) :7005-7007

[10] Michael addition of indoles to β-nitrostyrenes catalyzed by HY zeolite under solvent-free conditions [J].

Jeganathan, Mariappan ;

Kanagaraj, Kuppusamy ;

Dhakshinamoorthy, Amarajothi ;

Pitchumani, Kasi .

TETRAHEDRON LETTERS, 2014, 55 (13) :2061-2064

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