Furfuryl Vinyl Ethers in [4+2]-Cycloaddition Reactions

被引：6
|
作者：
Oparina, L. A. [1 ]
Vysotskaya, O. V. [1 ]
Stepanov, A. V. [1 ]
Ushakov, I. A. [1 ]
Apartsin, K. A. [1 ]
Gusarova, N. K. [1 ]
Trofimov, B. A. [1 ]
机构：
[1] Russian Acad Sci, Favorskii Irkutsk Inst Chem, Siberian Branch, Ul Favorskogo 1, Irkutsk 664033, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 53卷 / 02期
关键词：
SUPERBASIC CATALYTIC-SYSTEMS; NUCLEOPHILIC-ADDITION; FURAN; ACETYLENES; ALCOHOLS; ANALOGS; SERIES;
D O I：
10.1134/S1070428017020105
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
For the first time [4+2]-cycloaddition reactions were carried out between furfuryl vinyl ethers and typical dienophiles and heterodienes proceeding in uncatalyzed conditions and resulting in previously unknown heterocyclic systems containing either free vinyloxy groups or furfuryl substituents. With maleic anhydride and maleimide furfuryl vinyl ethers afforded 1-(vinyloxyalkyl)tricyclodec-8-ene-3,5-diones in up to 72% yields, and with N-benzylideneaniline or acrolein the corresponding functionally substituted tetrahydroquinolines (yield up to 65%) or 3,4-dihydropyrans (yield 23-50%) were obtained.
引用
收藏
页码：203 / 209
页数：7
相关论文
共 50 条
  • [1] Furfuryl vinyl ethers in [4+2]-cycloaddition reactions
    L. A. Oparina
    O. V. Vysotskaya
    A. V. Stepanov
    I. A. Ushakov
    K. A. Apartsin
    N. K. Gusarova
    B. A. Trofimov
    Russian Journal of Organic Chemistry, 2017, 53 : 203 - 209
  • [2] Further investigations into the preparation and [4+2] cycloaddition reactions of vinyl norcaradiene derivatives
    Buttle, LA
    Morris, JC
    Mander, LN
    ARKIVOC, 2003, : 118 - 134
  • [3] CYCLOADDITION 4+2 REACTIONS OF LEVOGLUCOSENONE
    WARD, DD
    SHAFIZADEH, F
    CARBOHYDRATE RESEARCH, 1981, 95 (02) : 155 - 176
  • [4] [4+2] CYCLOADDITION REACTIONS OF TRIARYLPHOSPHAALKENES
    VANDERKNAAP, TA
    KLEBACH, TC
    VISSER, F
    LOURENS, R
    BICKELHAUPT, F
    TETRAHEDRON, 1984, 40 (06) : 991 - 997
  • [5] THE (4+2) CYCLOADDITION OF AZODICARBOXYLATES AND CYCLIC VINYL ETHERS - APPLICATION TO THE SYNTHESIS OF 2-AMINO DISACCHARIDES
    LEBLANC, Y
    FITZSIMMONS, BJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 200 : 61 - CARB
  • [6] Organocatalytic Asymmetric [4+2] Cycloaddition Reactions
    Wang Chun
    Liu Weihua
    Zhou Xin
    Li Yuemin
    Li Yunpeng
    PROGRESS IN CHEMISTRY, 2009, 21 (09) : 1857 - 1868
  • [7] THE [4+2] CYCLOADDITION OF AZODICARBOXYLATES AND CYCLIC VINYL ETHERS - APPLICATION TO THE SYNTHESIS OF SIMPLE AND COMPLEX 2-AMINOSACCHARIDES
    LEBLANC, Y
    LABELLE, M
    ACS SYMPOSIUM SERIES, 1992, 494 : 81 - 96
  • [8] UTILIZATION OF VINYLSILANES IN [4+2] CYCLOADDITION REACTIONS
    PADWA, A
    MACDONALD, JG
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (19): : 3189 - 3195
  • [9] MICROWAVE [4+2]CYCLOADDITION REACTIONS OF GLYOXAL DERIVATIVES
    STAMBOULI, A
    CHASTRETTE, M
    SOUFIAOUI, M
    TETRAHEDRON LETTERS, 1991, 32 (14) : 1723 - 1724
  • [10] ELECTRON FACTORS IN THE REACTIONS OF (4+2)-CYCLOADDITION OF PHOSPHAALKENES
    PENKOVSKY, VV
    KHARCHENKO, VI
    ALEKSEIKO, LN
    TEORETICHESKAYA I EKSPERIMENTALNAYA KHIMIYA, 1991, 27 (04): : 462 - 466
12345