Clay catalyzed chemoselective Michael type addition of aliphatic amines to α,β-ethylenic compounds

被引：137

作者：

Shaikh, NS ^{[1
]}

Deshpande, VH ^{[1
]}

Bedekar, AV ^{[1
]}

机构：

[1] Natl Chem Lab, Div Organ Chem Technol, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON | 2001年 / 57卷 / 43期

关键词：

heterogeneous catalyst; Michael addition reaction; amines; alpha; beta-ethylenic compounds;

D O I：

10.1016/S0040-4020(01)00911-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Application of acidic clays as heterogeneous catalysts for the Michael type addition reaction of aliphatic amines to alpha,beta -ethylenic compounds is presented. Aromatic amines do not participate in this transformation. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：9045 / 9048

页数：4

共 41 条

[1] ORALLY ACTIVE AND POTENT INHIBITORS OF GAMMA-AMINOBUTYRIC ACID UPTAKE [J].

ALI, FE ;

BONDINELL, WE ;

DANDRIDGE, PA ;

FRAZEE, JS ;

GARVEY, E ;

GIRARD, GR ;

KAISER, C ;

KU, TW ;

LAFFERTY, JJ ;

MOONSAMMY, GI ;

OH, HJ ;

RUSH, JA ;

SETLER, PE ;

STRINGER, OD ;

VENSLAVSKY, JW ;

VOLPE, BW ;

YUNGER, LM ;

ZIRKLE, CL .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (05) :653-660

[2] Synthesis of novel GABA uptake inhibitors. 4. Bioisosteric transformation and successive optimization of known GABA uptake inhibitors leading to a series of potent anticonvulsant drug candidates [J].

Andersen, KE ;

Sorensen, JL ;

Huusfeldt, PO ;

Knutsen, LJS ;

Lau, J ;

Lundt, BF ;

Petersen, H ;

Suzdak, PD ;

Swedberg, MDB .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (21) :4281-4291

[3] Clay catalyzed acetonation: A simple method for the preparation of isopropylidene carbohydrates [J].

Asakura, J ;

Matsubara, Y ;

Yoshihara, M .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1996, 15 (02) :231-239

[4] Removal of acetal, silyl, and 4,4'-dimethoxytrityl protecting groups from hydroxyl functions of carbohydrates and nucleosides with clay in aqueous methanol [J].

Asakura, J ;

Robins, MJ ;

Asaka, Y ;

Kim, TH .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :9026-9027

[5] Natural kaolinitic clay: a remarkable reusable solid catalyst for the selective cleavage of thioacetals without solvent [J].

Bandgar, BP ;

Kasture, SP .

GREEN CHEMISTRY, 2000, 2 (04) :154-156

[6]

BENAYED T, 1995, TETRAHEDRON, V35, P9633

[7] CATALYSIS OF THE SPECIFIC MICHAEL ADDITION - THE EXAMPLE OF ACRYLATE ACCEPTORS [J].

CABRAL, J ;

LASZLO, P ;

MAHE, L ;

MONTAUFIER, MT ;

RANDRIAMAHEFA, SL .

TETRAHEDRON LETTERS, 1989, 30 (30) :3969-3972

[8] Novel 3-aminomethyl- and 4-aminopiperidine analogues of 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazines: Synthesis and evaluation as dopamine transporter ligands [J].

Choi, SW ;

Elmaleh, DR ;

Hanson, RN ;

Fischman, AJ .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (02) :205-213

[9] SYNTHESIS OF 1,2,3,4-TETRAHYDRO-5H-[1]BENZOPYRANO[3,4-C]PYRIDIN-5-ONES .1. 3-UNSUBSTITUTED COMPOUNDS [J].

CONNOR, DT ;

UNANGST, PC ;

SCHWENDER, CF ;

SORENSON, RJ ;

CARETHERS, ME ;

PUCHALSKI, C ;

BROWN, RE .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (05) :1557-1559

[10]

CORNELIS A, 1994, SYNLETT, P155

← 1 2 3 4 5 →