Efficient synthesis of the 3-benzazepine framework via intramolecular heck reductive cyclization

被引：100

作者：

Donets, Pavel A. ^{[1
]}

Van der Eycken, Erik V. ^{[1
]}

机构：

[1] Univ Leuven, Lab Organ & Microwave Assisted Chem, Dept Chem, B-3001 Louvain, Belgium

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 16期

关键词：

D O I：

10.1021/ol071079g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A microwave-assisted protocol based on reductive Heck reaction was developed for regio- and stereoselective construction of the 3-benzazepine core.

引用

页码：3017 / 3020

页数：4

共 27 条

[1] Late N-methyl-D-aspartate receptor blockade rescues hippocampal neurons from excitotoxic stress and death after 4-aminopyridine-induced epilepsy
Ayala, GX
Tapia, R
[J]. EUROPEAN JOURNAL OF NEUROSCIENCE, 2005, 22 (12) : 3067 - 3076
[2] Cyclic sulfamidates as lactam precursors. An efficient asymmetric synthesis of (-)-aphanorphine
Bower, JF
Szeto, P
Gallagher, T
[J]. CHEMICAL COMMUNICATIONS, 2005, (46) : 5793 - 5795
[3] Cyclic sulfamidates as versatile lactam precursors. An evaluation of synthetic strategies towards (-)-aphanorphine
Bower, John F.
Szeto, Peter
Gallagher, Timothy
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (01) : 143 - 150
[4] Asymmetric synthesis of 3-substituted isoindolinones: Application to the total synthesis of (+)-lennoxamine
Comins, DL
Schilling, S
Zhang, YC
[J]. ORGANIC LETTERS, 2005, 7 (01) : 95 - 98
[5] Total synthesis of (±)-lennoxamine and (±)-aphanorphine by intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins
Fuchs, JR
Funk, RL
[J]. ORGANIC LETTERS, 2001, 3 (24) : 3923 - 3925
[6] Herrmann W. A., 1995, ANGEW CHEM, V107, P1989
[7] Palladacycles: Efficient new catalysts for the Heck vinylation of aryl halides
Herrmann, WA
Brossmer, C
Reisinger, CP
Riermeier, TH
Ofele, K
Beller, M
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (08) : 1357 - 1364
[8] PALLADACYCLES AS STRUCTURALLY DEFINED CATALYSTS FOR THE HECK OLEFINATION OF CHLOROARENES AND BROMOARENES
HERRMANN, WA
BROSSMER, C
OFELE, K
REISINGER, CP
PRIERMEIER, T
BELLER, M
FISCHER, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17): : 1844 - 1848
[9] Enantioselective synthesis of (+)-aphanorphine by means of samarium diiodide promoted reductive carbon-nitrogen bond-cleavage reaction
Katoh, N
Inoue, H
Suzuki, A
Honda, T
[J]. SYNLETT, 2005, (18) : 2820 - 2822
[10] Use of the triflamide group for Friedel-crafts acylation of N-(beta-phenethyl)amino acids to 3-benzazepine derivatives
Kawase, M
Motohashi, N
Niwa, M
Nozaki, M
[J]. HETEROCYCLES, 1997, 45 (06) : 1121 - 1129

← 1 2 3 →