A novel base-promoted synthesis of β-indolylketones via a three-component condensation under ultrasonic irradiation

被引：42

作者：

Shen, ZL ^{[1
]}

Ji, SJ ^{[1
]}

Wang, SY ^{[1
]}

Zeng, XF ^{[1
]}

机构：

[1] Suzhou Univ, Coll Chem & Chem Engn, Key Lab Organ Synth Jiangsu Prov, Suzhou 215006, Peoples R China

来源：

TETRAHEDRON | 2005年 / 61卷 / 44期

基金：

中国国家自然科学基金;

关键词：

indole; beta-indolylketone; one-pot synthesis; ultrasound;

D O I：

10.1016/j.tet.2005.08.042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient, efficient, and practical method for the synthesis of beta-indolylketones via a condensation of indole, aromatic aldchydes, and deoxybenzoin under ultrasonic irradiation was described. It provided a novel base-promoted approach for the one-pot synthesis of beta-indolylketones. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：10552 / 10558

页数：7

共 64 条

[1] New versatile route to the synthesis of tetrahydro-β-carbolines and tetrahydro-pyrano[3,4-b]indoles via an intramolecular Michael addition catalyzed by InBr3 [J].

Agnusdei, M ;

Bandini, M ;

Melloni, A ;

Umani-Ronchi, A .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :7126-7129

[2] Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3 [J].

Alam, MM ;

Varala, R ;

Adapa, SR .

TETRAHEDRON LETTERS, 2003, 44 (27) :5115-5119

[3] SODIUM PERCARBONATE (SPC) AS A HYDROGEN-PEROXIDE SOURCE FOR ORGANIC-SYNTHESIS [J].

ANDO, T ;

CORK, DG ;

KIMURA, T .

CHEMISTRY LETTERS, 1986, (05) :665-666

[4]

[Anonymous], 1996, CHEM INDOLES

[5] Multiple-component condensation strategies for combinatorial library synthesis [J].

Armstrong, RW ;

Combs, AP ;

Tempest, PA ;

Brown, SD ;

Keating, TA .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131

[6] Sequential one-pot InBr3-catalyzed 1,4-then 1,2-nucleophilic addition to enones [J].

Bandini, M ;

Cozzi, PG ;

Giacomini, M ;

Melchiorre, P ;

Selva, S ;

Umani-Ronchi, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3700-3704

[7] The Michael addition of indoles to α,β-unsaturated ketones catalyzed by CeCl3•7H2O-NaI combination supported on silica gel [J].

Bartoli, G ;

Bartolacci, M ;

Bosco, M ;

Foglia, G ;

Giuliani, A ;

Marcantoni, E ;

Sambri, L ;

Torregiani, E .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4594-4597

[8] Ultrasound-assisted nucleophilic substitution reaction of t-alkyl halides with zinc and titanium thiocyanate [J].

Bettadaiah, BK ;

Gurudutt, KN ;

Srinivas, P .

SYNTHETIC COMMUNICATIONS, 2003, 33 (13) :2293-2299

[9]

Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO

[10]

2-A

← 1 2 3 4 5 6 7 →