Diels-Alder modification of monoterpenes and Alder-ene synthesis involving 3-methyl-3-cyanocyclopropene

被引:4
|
作者
Ashirov, R. V.
Appolonova, S. A.
Plemenkov, V. V.
机构
[1] Kazan State Med Univ, Kazan 420012, Russia
[2] FSUE Antidoping Ctr, Moscow 105005, Russia
关键词
monoterpenes; Diels-Alder reaction; Alder-ene synthesis; 3-methyl-3-cyanocyclopropene;
D O I
10.1007/s10600-006-0174-7
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Monoterpene derivatives with a cyclopropane moiety in the molecule were prepared by reactions of 3-methyl-3-cyanocyclopropene with several monoterpenes and terpenoids (beta-myrcene, neoalloocimene, alloocimene, beta-pinene, carvone). They were formed using the Diels-Alder reaction, Alder-ene synthesis, conjugated Alder-ene addition, and Diels-Alder cyclization.
引用
收藏
页码:434 / 438
页数:5
相关论文
共 50 条
  • [1] Diels-Alder modification of monoterpenes and Alder-ene synthesis involving 3-methyl-3-cyanocyclopropene
    R. V. Ashirov
    S. A. Appolonova
    V. V. Plemenkov
    Chemistry of Natural Compounds, 2006, 42 : 434 - 438
  • [2] Alder-ene reaction of 3-methyl-3-cyanocyclopropene with monoterpenes
    Ashirov, Roman V.
    Balandina, Alsu A.
    Kharlamov, Sergey V.
    Appolonova, Svetlana A.
    Figadere, Bruno
    Latypov, Shamil K.
    Plemenkov, Vitali V.
    LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (09) : 670 - 673
  • [3] SYNTHESIS, STRUCTURE AND REACTIVITY OF CYCLOPROPANES AND CYCLOPROPENES .18. 3-METHYL-3-CYANOCYCLOPROPENE IN THE DIELS-ALDER REACTION
    LATYPOVA, MM
    PLEMENKOV, VV
    KALININA, VN
    BOLESOV, IG
    ZHURNAL ORGANICHESKOI KHIMII, 1984, 20 (03): : 542 - 548
  • [4] Stereochemistry of Diels-Alder attachment of 3-methyl-3-cyanocyclopropene to 1,4-disubstituted butadienes.: ekso-syn-orientation
    Rul, SV
    Plemenkov, VV
    Gubaidullin, AT
    Litvinov, IA
    Kataeva, ON
    Appolonova, SA
    ZHURNAL ORGANICHESKOI KHIMII, 1999, 35 (08): : 1151 - 1156
  • [5] Consecutive Rh(I)-catalyzed Alder-ene/Diels-Alder/Diels-Alder reaction sequence affording rapid entry to polycyclic compounds
    Brummond, KM
    You, LF
    TETRAHEDRON, 2005, 61 (26) : 6180 - 6185
  • [6] 1-Methylcycloprop-2-ene-1-carbonitrile in tandem alder-ene and diels-alder reactions
    Lodochnikova, O. A.
    Ashirov, R. V.
    Appolonova, S. A.
    Litvinov, I. A.
    Plemenkov, V. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (01) : 49 - 53
  • [7] 1-Methylcycloprop-2-ene-1-carbonitrile in tandem alder-ene and diels-alder reactions
    O. A. Lodochnikova
    R. V. Ashirov
    S. A. Appolonova
    I. A. Litvinov
    V. V. Plemenkov
    Russian Journal of Organic Chemistry, 2010, 46 : 49 - 53
  • [8] Diels-Alder reaction of vinylapopinenes with 3-methyl-3-cyanocyclopropene as the route to synthetic terpenoids with pinene-carene skeleton. Molecular structure of adducts
    Plemenkov, VV
    Rul, SV
    Gubaidullin, AT
    Litvinov, IA
    Karaseva, IP
    Nuretdinov, IA
    ZHURNAL ORGANICHESKOI KHIMII, 1998, 34 (07): : 1023 - 1025
  • [9] A Molecular Electron Density Theory Study of the Competitiveness of Polar Diels-Alder and Polar Alder-ene Reactions
    Domingo, Luis R.
    Rios-Gutierrez, Mar
    Perez, Patricia
    MOLECULES, 2018, 23 (08):
  • [10] ISOMERISM IN THE DIELS-ALDER REACTION .3. THE BROMINATION OF THE DIELS-ALDER ADDUCT, NORBORNYLENE
    KWART, H
    KAPLAN, L
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (16) : 4072 - 4077