Multicomponent synthesis of polysubstituted dihydroquinoline derivatives

被引：18
作者：
Yu, Yan
Tu, Man-Su
Jiang, Bo [1 ]
Wang, Shu-Liang
Tu, Shu-Jiang
机构：
[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 211116, Peoples R China
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 38期
基金：
美国国家科学基金会;
关键词：
Microwave (MW)-assisted synthesis; Polysubstituted hydroquinoline; Multicomponent domino reactions; DOMINO REACTION; EFFICIENT SYNTHESIS; AROMATIC-AMINES; GLYCINE-SITE; WATER; QUINOLINES; REARRANGEMENT; ANILINES; ACCESS; AGENTS;
D O I：
10.1016/j.tetlet.2012.07.008
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of new poly-functionalized dihydroquinoline derivatives (26 examples) were synthesized via three-component reactions of aldehydes (1 equiv) and 1-arylethylidenemalononitriles (2 equiv) in ethylene glycol using NaOH as a base promoter under microwave irradiation. During these reaction processes, the domino construction of dihydroquinoline skeleton with concomitant formation of two new cycles was readily achieved in a one-pot operation and in an intermolecular manner. (C) 2012 Elsevier Ltd. All rights reserved.
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收藏
页码：5071 / 5075
页数：5
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  • [51] Cu(OTf)2/Et3N-promoted cyclocondensation of activated α-methylene alkenes and nitroolefins: a novel one-pot synthesis of polysubstituted benzenes
    Su, Weike
    Ding, Kai
    Chen, Zhiwei
    [J]. TETRAHEDRON LETTERS, 2009, 50 (06) : 636 - 639
  • [52] First asymmetric synthesis of quinoline derivatives by inverse electron demand (IED) Diels-Alder reaction using chiral Ti(IV) complex
    Sundararajan, G
    Prabagaran, N
    Varghese, B
    [J]. ORGANIC LETTERS, 2001, 3 (13) : 1973 - 1976
  • [53] INTRAMOLECULAR DIELS-ALDER REACTIONS OF 1,2,4-TRIAZINES - SYNTHESIS OF 2,3-CYCLOPENTENOPYRIDINES AND 5,6,7,8-TETRAHYDROQUINOLINES
    TAYLOR, EC
    MACOR, JE
    FRENCH, LG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) : 1807 - 1812
  • [54] A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): its application to the synthesis of key intermediates for anti-malarial agents
    Theeraladanon, C
    Arisawa, M
    Nishida, A
    Nakagawa, M
    [J]. TETRAHEDRON, 2004, 60 (13) : 3017 - 3035
  • [55] Intrarnolecular hetero Diels-Alder (Povarov) approach to the synthesis of the alkaloids luotonin A and camptothecin
    Twin, H
    Batey, RA
    [J]. ORGANIC LETTERS, 2004, 6 (26) : 4913 - 4916
  • [56] Rhodium(I)-catalyzed hydroaminomethylation of 2-isopropenylanilines as a novel route to 1,2,3,4-tetrahydroquinolines
    Vieira, Tiago O.
    Alper, Howard
    [J]. CHEMICAL COMMUNICATIONS, 2007, (26) : 2710 - 2711
  • [57] STABILISOTOP MARKIERTE VERBINDUNGEN .2. UNTERSUCHUNG DER SKAUPSCHEN CHINOLINSYNTHESE MIT HILFE VON 15N1,2
    WAHREN, M
    [J]. TETRAHEDRON, 1964, 20 (12) : 2773 - &
  • [58] Asymmetric cycloadditions of palladium-polarized aza-o-xylylenes
    Wang, Chao
    Tunge, Jon A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (26) : 8118 - +
  • [59] Multicomponent Synthesis of Poly-Substituted Benzo[a]pyrano-[2,3-c]phenazine Derivatives under Microwave Heating
    Wang, Shu-Liang
    Wu, Fei-Yue
    Cheng, Chuang
    Zhang, Ge
    Liu, Yin-Ping
    Jiang, Bo
    Shi, Feng
    Tu, Shu-Jiang
    [J]. ACS COMBINATORIAL SCIENCE, 2011, 13 (02) : 135 - 139
  • [60] A simple method for synthesis of 5-CF3 substituted dienamides via rearrangement of 2H-pyran derivatives
    Wang, Xiao-Wei
    Li, Peng
    Xiao, Hua
    Zhu, Shi-Zheng
    Zhao, Gang
    [J]. TETRAHEDRON, 2011, 67 (39) : 7618 - 7621
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