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
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
收藏
页码:8453 / 8456
页数:4
相关论文
共 43 条
[1]   CHEMISTRY OF FORMAMIDE ACETALS [J].
ABDULLA, RF ;
BRINKMEYER, RS .
TETRAHEDRON, 1979, 35 (14) :1675-1735
[2]  
BARALDI PG, 1983, SYNTHESIS-STUTTGART, P902
[3]   Chiral cyclic beta-amino esters .1. Synthesis by diastereospecific alkylation. [J].
Bardou, A ;
Celerier, JP ;
Lhommet, G .
TETRAHEDRON LETTERS, 1997, 38 (49) :8507-8510
[4]   ASYMMETRIC FORMATION OF QUATERNARY CENTERS THROUGH AZA-ANNULATION OF CHIRAL BETA-ENAMINO ESTERS WITH ACRYLATE DERIVATIVES [J].
BARTA, NS ;
BRODE, A ;
STILLE, JR .
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 [J].
BARTOLI, G ;
CIMARELLI, C ;
DALPOZZO, R ;
PALMIERI, G .
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 [J].
BARTOLI, G ;
CIMARELLI, C ;
MARCANTONI, E ;
PALMIERI, G ;
PETRINI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5328-5335
[7]   Solvent free oxidation of β,β-disubstituted enamines under microwave irradiation [J].
Benhaliliba, H ;
Derdour, A ;
Bazureau, JP ;
Texier-Boullet, F ;
Hamelin, 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 [J].
Benovsky, P ;
Stille, JR .
TETRAHEDRON LETTERS, 1997, 38 (49) :8475-8478
[9]   Chiral cyclic beta-amino esters .2. Synthesis by diastereoselective reduction of enamino esters [J].
Blot, J ;
Bardou, A ;
Bellec, C ;
FargeauBellassoued, MC ;
Celerier, JP ;
Lhommet, G ;
Gardette, D ;
Gramain, JC .
TETRAHEDRON LETTERS, 1997, 38 (49) :8511-8514
[10]  
BRAM G, 1987, PREPARATIVE CHEM USI, P387