A copper(II)-catalyzed, sequential Michael-aldol reaction for the preparation of 1,2-dihydroquinolines

被引：15
|
作者：
Wagner, Anna M.
Knezevic, Claire E.
Wall, Jessica L.
Sun, Victoria L.
Buss, Joshua A.
Allen, LeeAnn T.
Wenzel, Anna G. [1 ]
机构：
[1] Claremont Mckenna Coll, Keck Sci Dept, Claremont, CA 91711 USA
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 07期
基金：
美国国家科学基金会;
关键词：
Heterocycles; Lewis acid catalysis; Michael-aldol reaction; Acetonitrile; Small-molecule synthesis; ALPHA; BETA-UNSATURATED N-ACYLPYRROLES; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; DIELS-ALDER REACTION; CONVENIENT SYNTHESIS; CONJUGATE ADDITION; FACILE SYNTHESIS; DERIVATIVES; ACID; METATHESIS; QUINOLINES;
D O I：
10.1016/j.tetlet.2011.12.017
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper(II)-catalyzed, sequential Michael addition-aldol condensation reaction of N-carboxybenzyl-protected aminobenzaldehyde with various alpha,beta-unsaturated N-acyl pyrroles is described. Substrate scope was found to include both aryl and aliphatic N-acyl pyrroles as the Michael acceptors, and isolated product yields as high as 93% were observed. The use of acetonitrile as the reaction solvent proved to be crucial for catalysis, both to function as a labile ligand for copper, as well as an agent to minimize hydrolytic catalyst poisoning. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：833 / 836
页数：4
相关论文
共 50 条
  • [1] Convergent approach to the preparation of 1,2-dihydroquinolines via a tandem Michael-aldol reaction
    Wagner, Anna
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
  • [2] Tandem Michael-aldol reactions for the preparation of dihydroquinolines
    Wenzel, Anna G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [3] An acid-catalyzed Michael-aldol reaction
    Reingold, ID
    Bowerman, C
    John, M
    Walters, RS
    Daglen, BC
    Butterfield, AM
    Gembicky, M
    TETRAHEDRON LETTERS, 2006, 47 (10) : 1653 - 1655
  • [4] THE TANDEM MICHAEL-ALDOL REACTION CATALYZED BY TRITYL PERCHLORATE
    MUKAIYAMA, T
    KOBAYASHI, S
    HETEROCYCLES, 1987, 25 : 205 - 211
  • [5] Enzyme-catalyzed asymmetric domino aza-Michael/aldol reaction for the synthesis of 1,2-dihydroquinolines using pepsin from porcine gastric mucosa
    Xue-Dong Zhang
    Na Gao
    Zhi Guan
    Yan-Hong He
    Chinese Chemical Letters, 2016, 27 (06) : 964 - 968
  • [6] Enzyme-catalyzed asymmetric domino aza-Michael/aldol reaction for the synthesis of 1,2-dihydroquinolines using pepsin from porcine gastric mucosa
    Zhang, Xue-Dong
    Gao, Na
    Guan, Zhi
    He, Yan-Hong
    CHINESE CHEMICAL LETTERS, 2016, 27 (06) : 964 - 968
  • [7] 1,2-DIHYDROQUINOLINES IN FRIEDEL-CRAFTS REACTION
    LUGOVIK, BA
    YUDIN, LG
    KOST, AN
    DOKLADY AKADEMII NAUK SSSR, 1966, 170 (02): : 340 - &
  • [8] An Efficient Copper-Catalyzed Cyclocondensation of Anilines with Propargyl Alcohols Approach to 1,2-Dihydroquinolines
    Su, Ji
    Ju, Jia
    Hua, Ruimao
    CURRENT ORGANIC SYNTHESIS, 2012, 9 (02) : 273 - 277
  • [9] 1,2-DIHYDROQUINOLINES - PREPARATION AND ISOLATION AS INTERMEDIATES IN SYNTHESIS OF QUINOLINES
    DAUPHINEE, GA
    FORREST, TP
    CANADIAN JOURNAL OF CHEMISTRY, 1978, 56 (05) : 632 - 634
  • [10] RING EXPANSION REACTION OF 1,2-DIHYDROQUINOLINES TO 1-BENZAZEPINES
    SATO, Y
    KOJIMA, H
    SHIRAI, H
    HETEROCYCLES, 1975, 3 (12) : 1139 - 1139
12345