Novel pyridine catalysed reactions of dimethyl acetylenedicarboxylate (DMAD) and arylmethylidenemalononitriles: a stereoselective synthesis of highly substituted buta-1,3-dienes

被引:26
|
作者
Nair, V [1 ]
Devi, BR
Vidya, N
Menon, RS
Abhilash, N
Rath, NP
机构
[1] CSIR, Div Organ Chem, Trivandrum 695019, Kerala, India
[2] Univ Missouri, Dept Chem, St Louis, MO 63121 USA
关键词
pyridine; dimethyl acetylenedicarboxylate; dipoles;
D O I
10.1016/j.tetlet.2004.02.132
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A pyridine catalysed addition of dimethyl acetylenedicarboxylate to various arylmethylidenemalononitriles to afford highly substituted 1,3-butadienes with complete stereoselectivity is described. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3203 / 3205
页数:3
相关论文
共 50 条
  • [21] AROYLATION OF N-ALKYLMETHANIMINES - A SYNTHESIS OF NOVEL SUBSTITUTED 2-AZA-BUTA-1,3-DIENES
    ARMESTO, D
    ORTIZ, MJ
    PEREZOSSORIO, R
    TETRAHEDRON LETTERS, 1981, 22 (23) : 2203 - 2206
  • [22] SYNTHESIS OF 2-SUBSTITUTED BUTA-1,3-DIENES FROM 1,4-DICHLOROBUT-2-YNE VIA ORGANOBORANES
    HOSHI, M
    ARASE, A
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (22): : 2693 - 2700
  • [23] 1-(Triethoxysilyl)buta-1,3-dienes-New Building Blocks for Stereoselective Synthesis of Unsymmetrical (E,E)-1,4-Disubstituted 1,3-dienes
    Szudkowska-Fratczak, Justyna
    Taczala, Mariusz
    Pawluc, Piotr
    MATERIALS, 2015, 8 (11) : 7250 - 7256
  • [24] Highly stereoselective synthesis of substituted 1-pentafluorophenyl-1,3-dienes via arsonium ylides
    Shen, YC
    Wang, TL
    JOURNAL OF FLUORINE CHEMISTRY, 1997, 82 (02) : 139 - 141
  • [25] Three-Component Reaction of Dimethyl Malonate with α,β-Acetylenic Aldehydes and Amines. Synthesis of Push-Pull Buta-1,3-dienes
    Sokov, S. A.
    Odin, I. S.
    Zlotskii, S. S.
    Golovanov, A. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (10) : 1758 - 1763
  • [26] Assembling of 3,6-diazabicyclo[3.1.0]hexane framework in oxidative triflamidation of substituted buta-1,3-dienes
    Moskalik, Mikhail Yu.
    Astakhova, Vera V.
    Schilde, Uwe
    Sterkhova, Irina V.
    Shainyan, Bagrat A.
    TETRAHEDRON, 2014, 70 (45) : 8636 - 8641
  • [27] A HIGHLY STEREOSELECTIVE SYNTHESIS OF CYCLOPENTENE DERIVATIVES FROM 1,3-DIENES
    DANHEISER, RL
    MARTINEZDAVILA, C
    AUCHUS, RJ
    KADONAGA, JT
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1981, 181 (MAR): : 21 - ORGN
  • [28] Regioselective Synthesis of Trichloromethyl-Substituted Salicylates and Cyclohexenones by One-Pot Cyclizations of 1,3-Bis(trimethylsilyloxy)buta-1,3-dienes
    Reimann, Sebastian
    Bunescu, Alina
    Petrosyan, Andranik
    Sharif, Muhammad
    Erfle, Silke
    Mamat, Constantin
    Ghochikyan, Tariel V.
    Saghyan, Ashot S.
    Spannenberg, Anke
    Villinger, Alexander
    Langer, Peter
    HELVETICA CHIMICA ACTA, 2013, 96 (10) : 1955 - 1967
  • [29] A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes
    Hou, Chuan-Jin
    Schuppe, Alexander W.
    Knippel, James Levi
    Ni, Anton Z.
    Buchwald, Stephen L.
    ORGANIC LETTERS, 2021, 23 (22) : 8816 - 8821
  • [30] Stereoselective Synthesis of Highly Substituted 1,3-Dienes via "a la carte" Multifunctionalization of Borylated Dendralenes
    Rivera-Chao, Eva
    Fananas-Mastral, Martin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (31) : 16922 - 16927