Synthesis of Mannich type products via a three-component coupling reaction

被引：162

作者：

Pandey, G ^{[1
]}

Singh, RP ^{[1
]}

Garg, A ^{[1
]}

Singh, VK ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 12期

关键词：

D O I：

10.1016/j.tetlet.2005.01.118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of alkyl nitriles, acetyl chloride, aldehydes and beta-ketoesters or simple ketones was studied for the one-pot synthesis of beta-acetamido carbonyl compounds. It was observed that the reaction proceeds in the absence of Lewis acids. However, a Lewis acid catalyzes the reaction and several were tested. It was found that whereas Cu(OTf)(2) is suitable for the coupling of beta-ketoesters with aldehydes, Sc(OTf)(3) is the best for ketones. A possible mechanism is proposed based on the isolation and characterization of an intermediate. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2137 / 2140

页数：4

共 13 条

[1] 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

[2] Montmorillonite K10 clay:: An efficient catalyst for the one-pot stereoselective synthesis of β-acetanxido ketones [J].

Bahulayan, D ;

Das, SK ;

Iqbal, J .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (14) :5735-5738

[3]

Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO

[4]

2-U

[5] Design, synthesis, and evaluation of small-molecule libraries [J].

Ellman, JA .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :132-143

[6] Nickel-catalyzed cyclizations, couplings, and cycloadditions involving three reactive components [J].

Montgomery, J .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (07) :467-473

[7] 2-aryl-N-tosylazetidines as formal 1,4-dipoles for [4+2] cycloaddition reactions with nitriles:: An easy access to the tetrahydropyrimidine derivatives [J].

Prasad, BAB ;

Bisai, A ;

Singh, VK .

ORGANIC LETTERS, 2004, 6 (26) :4829-4831

[8] Synthesis of substituted imidazolines via [3+2]-cycloaddition of aziridines with nitriles [J].

Prasad, BAB ;

Pandey, G ;

Singh, VK .

TETRAHEDRON LETTERS, 2004, 45 (06) :1137-1141

[9] Cobalt-catalyzed one-pot three-component coupling route to β-acetamido carbonyl compounds:: A general synthetic protocol for γ-lactams [J].

Rao, IN ;

Prabhakaran, EN ;

Das, SK ;

Iqbal, J .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :4079-4082

[10]

Strecker A., 1850, Justus Liebigs Ann. Chem, V75, P27, DOI [DOI 10.1002/JLAC.18500750103, 10.1002/jlac.18500750103]

← 1 2 →