A new route to α-hetero β-enamino esters using a mild and convenient solvent-free process assisted by focused microwave irradiation

被引：15

作者：

Dahmani, Z ^{[1
]}

Rahmouni, M ^{[1
]}

Brugidou, R ^{[1
]}

Bazureau, JP ^{[1
]}

Hamelin, J ^{[1
]}

机构：

[1] Univ Rennes 1, CNRS, UMR Synth & ElectroSynth Organ 3 6510, F-35042 Rennes, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(98)01894-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New alpha-hetero beta-enamino esters 5 (X - NH, O, S) are obtained in good to excellent yields by transamination reactions from ethyl 3-dimethylamino acrylate 2(a-c) and various volatile amines 3(a-e) using solvent-free conditions assisted by focused microwave irradiation. Most of the alpha-hetero beta-enamino ester derivatives 3 present a (E)-s-cis/trans conformation. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8453 / 8456

页数：4

共 43 条

[1] CHEMISTRY OF FORMAMIDE ACETALS
ABDULLA, RF
BRINKMEYER, RS
[J]. TETRAHEDRON, 1979, 35 (14) : 1675 - 1735
[2] BARALDI PG, 1983, SYNTHESIS-STUTTGART, P902
[3] Chiral cyclic beta-amino esters .1. Synthesis by diastereospecific alkylation.
Bardou, A
Celerier, JP
Lhommet, G
[J]. TETRAHEDRON LETTERS, 1997, 38 (49) : 8507 - 8510
[4] ASYMMETRIC FORMATION OF QUATERNARY CENTERS THROUGH AZA-ANNULATION OF CHIRAL BETA-ENAMINO ESTERS WITH ACRYLATE DERIVATIVES
BARTA, NS
BRODE, A
STILLE, JR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) : 6201 - 6206
[5] A VERSATILE ROUTE TO BETA-ENAMINO ESTERS BY ACYLATION OF LITHIUM ENAMINES WITH DIETHYL CARBONATE OR BENZYL CHLOROFORMATE
BARTOLI, G
CIMARELLI, C
DALPOZZO, R
PALMIERI, G
[J]. TETRAHEDRON, 1995, 51 (31) : 8613 - 8622
[6] CHEMOSELECTIVE AND DIASTEREOSELECTIVE REDUCTION OF BETA-ENAMINO ESTERS - A CONVENIENT SYNTHESIS OF BOTH CIS-GAMMA-AMINO AND TRANS-GAMMA-AMINO ALCOHOLS AND BETA-AMINO ESTERS
BARTOLI, G
CIMARELLI, C
MARCANTONI, E
PALMIERI, G
PETRINI, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) : 5328 - 5335
[7] Solvent free oxidation of β,β-disubstituted enamines under microwave irradiation
Benhaliliba, H
Derdour, A
Bazureau, JP
Texier-Boullet, F
Hamelin, J
[J]. TETRAHEDRON LETTERS, 1998, 39 (07) : 541 - 542
[8] Aza-annulation as a versatile approach to the synthesis of non-benzodiazepene compounds for the treatment of sleep disorders
Benovsky, P
Stille, JR
[J]. TETRAHEDRON LETTERS, 1997, 38 (49) : 8475 - 8478
[9] Chiral cyclic beta-amino esters .2. Synthesis by diastereoselective reduction of enamino esters
Blot, J
Bardou, A
Bellec, C
FargeauBellassoued, MC
Celerier, JP
Lhommet, G
Gardette, D
Gramain, JC
[J]. TETRAHEDRON LETTERS, 1997, 38 (49) : 8511 - 8514
[10] BRAM G, 1987, PREPARATIVE CHEM USI, P387

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