Reaction of dialkyl 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylates with aliphatic amines

被引：0
|
作者：
Gein, V. L. [1 ]
Nosova, N. V. [1 ]
Prusakova, A. S. [1 ]
Vakhrin, M. I. [1 ]
Kriven'ko, A. P. [2 ]
机构：
[1] Perm State Pharmaceut Acad, Perm 614990, Russia
[2] Saratov NG Chernyshevskii State Univ, Saratov, Russia
来源：
RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2008年 / 78卷 / 12期
关键词：
Dicarboxylates; Tryptamine; Benzylamine; Diallyl; Phenethylamine;
D O I：
10.1134/S1070363208120116
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Benzylamine, phenethylamine, and homoveratrylamine reacted with dialkyl 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylates at the endocyclic carbonyl group with conservation of the enolic hydroxy group to give dialkyl 4-alkylamino-2-aryl-6-hydroxy-6-methylcyclohex-3-ene-1,3-dicarboxylates. The reaction of dimethyl 4-hydroxy-4-methyl-6-oxo-2-phenylcyclohexane-1,3-dicarboxylate with tryptamine was accompanied by dehydration with formation of dimethyl 4-[2-(1H-indol-3-yl)ethylamino]-6-methyl-2-phenylcyclohexa-3,5-diene-1,3-dicarboxylate, presumably due to basic properties of the indole nitrogen atom.
引用
收藏
页码：2357 / 2362
页数：6
相关论文
共 50 条
  • [31] (1R*, 2R*, 3S*, 4R*)-Diethyl4-hydroxy 4-methyl-2-(4-methylphenyl)-6- oxocyclohexane-1,3-dicarboxylate
    Ismiev, Arif I.
    Gadirova, Narmina A.
    Hajiyeva, Kushvar E.
    Askerov, Rizvan K.
    Potekhin, Konstantin A.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O734 - +
  • [32] 1,3-Dialkyl-5-hydroxy-2-thioxoimidazolidin-4-one
    Kuhn, Norbert
    Maichle-Moessmer, Caecilia
    Steimann, Manfred
    Walker, Isabel
    Zeller, Klaus-Peter
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2010, 65 (04): : 533 - 536
  • [33] 2-[HYDROXY(DIALKYL)METHYL]-4-ARYL-6,6-DISUBSTITUTED 4,5-DIHYDRO-6H-1,3,4-OXADIAZINONES-5
    GLUSHKOV, VA
    BERDINSKII, IS
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1984, (07): : 896 - 897
  • [34] Reaction of methyl 6-aryl-5-acetyl-3,6-dihydrotetrazolo[1,5-a]pyrimidine-4-carboxylates with ammonia and aliphatic amines
    Gein, V. L.
    Zamaraeva, T. M.
    Panova, O. S.
    Nasakin, O. E.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (08) : 1174 - 1176
  • [35] Reaction of methyl 6-aryl-5-acetyl-3,6- dihydrotetrazolo[1,5-a]pyrimidine-4-carboxylates with ammonia and aliphatic amines
    V. L. Gein
    T. M. Zamaraeva
    O. S. Panova
    O. E. Nasakin
    Russian Journal of Organic Chemistry, 2015, 51 : 1174 - 1176
  • [36] REACTION OF 3,4,5,6-TETRAHYDRO-6-HYDROXY-4,4,6-TRIMETHYL-1,3-THIAZINE-2-THIONE WITH PRIMARY AMINES
    SCHWEIGER, K
    FUCHSGRUBER, A
    ZIGEUNER, G
    MONATSHEFTE FUR CHEMIE, 1977, 108 (01): : 257 - 263
  • [37] Isoquinoline-Catalyzed Reaction between 4-Hydroxycoumarin or 4-Hydroxy-6-methylpyran-1-one and Dialkyl Acetylene Dicarboxylates: Synthesis of Coumarin and Pyranopyrane Derivatives
    Anary-Abbasinejad, Mohammad
    Anaraki-Ardakani, Hossein
    Mosslemin, Mohammad Hossein
    Khavasi, Hamid Reza
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2010, 21 (02) : 319 - U212
  • [38] Reaction of 2-aryl(methyl)-4-cyano-5-hydrazino-1,3-oxazoles with aryl isothiocyanates
    Shablykin, O. V.
    Golovchenko, A. V.
    Brovarets, V. S.
    Drach, B. S.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2007, 77 (05) : 932 - 935
  • [39] Reaction of 4-oxocyclohexane-1,1,2,2-tetracarbonitriles and 5-hydroxy-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles with amines
    Sheverdov, VP
    Ershov, OV
    Efimov, RN
    Nasakin, OE
    Firgang, SI
    Tafeenko, VA
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2004, 74 (05) : 744 - 751
  • [40] Reaction of 2-aryl(methyl)-4-cyano-5-hydrazino-1,3-oxazoles with aryl Isothiocyanates
    O. V. Shablykin
    A. V. Golovchenko
    V. S. Brovarets
    B. S. Drach
    Russian Journal of General Chemistry, 2007, 77 : 932 - 935
12345