One-pot synthesis of α-bromoesters and ketones from β-ketoesters and diketones using supported reagents system

被引：15

作者：

Aoyama, T ^{[1
]}

Takido, T

Kodomari, M

机构：

[1] Nihon Univ, Coll Sci & Technol, Dept Mat & Appl Chem, Chiyoda Ku, Tokyo 1018308, Japan

[2] Shibaura Inst Technol, Dept Appl Chem, Minato Ku, Tokyo 1088548, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 09期

关键词：

D O I：

10.1016/j.tetlet.2004.01.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient method has been developed for the synthesis of alpha-bromoesters and ketones from beta-ketoesters and diketones in one pot using a supported reagents system, CuBr2/Al2O3-Na2CO3/Al2O3, in which beta-ketoester reacts first with CuBr2/ Al2O3 and the product, alpha-bromo-beta-ketoester, reacts with Na2CO3/Al2O3 to give the final product, alpha-bromoesters in good yields. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1873 / 1876

页数：4

共 19 条

[1] SYNTHESES OF HETEROCYCLIC FUSED THIAZOLE ACETIC-ACIDS .2. [J].

BELL, SC ;

WEI, PHL .

JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (04) :524-530

[2] CHROMIUM(II) CHLORIDE - A NEW REAGENT FOR CROSS-ALDOL REACTIONS [J].

DUBOIS, JE ;

AXIOTIS, G ;

BERTOUNESQUE, E .

TETRAHEDRON LETTERS, 1985, 26 (36) :4371-4372

[3]

Favorskii A. E., 1913, J PRAKT CHEM, V88, P658

[4] A HIGHLY STEREOSELECTIVE SYNTHESIS OF RACEMIC JUVENILE HORMONE [J].

JOHNSON, WS ;

LI, TT ;

FAULKNER, DJ ;

CAMPBELL, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (22) :6225-&

[5] One-pot synthesis of 2-aminothiazoles using supported reagents [J].

Kodomari, M ;

Aoyama, T ;

Suzuki, Y .

TETRAHEDRON LETTERS, 2002, 43 (09) :1717-1720

[6] SELECTIVE NUCLEAR HALOGENATION OF POLYMETHYLBENZENES WITH ALUMINA-SUPPORTED COPPER(II) HALIDES [J].

KODOMARI, M ;

SATOH, H ;

YOSHITOMI, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (11) :4149-4150

[7]

Kunckell F., 1901, CHEM BER, V34, P637

[8] A new preparative route to organic halides from alcohols via the reduction of polyhalomethanes [J].

Leonel, E ;

Paugam, JP ;

Nedelec, JY .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :7061-7064

[9]

LOHRISCH HJ, 1986, LIEBIGS ANN CHEM, P177

[10] A ONE-POT PREPARATION OF ALPHA-HALO-CARBONYL AND ALPHA-HALO-SULFONYL COMPOUNDS BY HALO-DEACYLATION [J].

MIGNANI, G ;

MOREL, D ;

GRASS, F .

TETRAHEDRON LETTERS, 1987, 28 (45) :5505-5508

← 1 2 →