Synthesis and conversions of substituted 4,5-dihydro-3H-spiro[benz-2-azepine-3,1′-cyclohexanes]

被引:0
|
作者
Varlamov A.V. [1 ]
Zubkov F.I. [1 ]
Lazareva E.V. [1 ]
Chernyshev A.I. [1 ]
Grudinin D.G. [1 ]
机构
[1] Russian Peoples Friendship University
关键词
Benz-2-azepines; Cyclic imines; Cycloaddition; Oxidation; Phase-transfer catalysis;
D O I
10.1023/A:1013805812281
中图分类号
学科分类号
摘要
On oxidizing substituted 1,2,4,5-tetrahydro-3H-spiro[benz-2-azepine-3,1′-cyclohexanes]with potassium permanganate under phase-transfer catalysis conditions the corresponding 4,5-dihydro derivatives are formed in quantitative yield. By the action of allyl- and benzylmagnesium halides 5-methyl-4,5-dihydro-3H-spiro[benz-2-azepine-3,1′-cyclohexane] is converted into 5-methyl-1,2,4,5- tetrahydro-1-allyl(benzyl)-3H-spiro[benz-2-azepine-3,1′-cyclohexane], and by reaction with phenoxyketene and dichlorocarbene into the corresponding 2-oxoazetidino[4,1-a]- and 1,1-dichloroaziridino[3,1-a]benz-2-azepines.
引用
收藏
页码:1251 / 1257
页数:6
相关论文
共 50 条
  • [31] Synthesis of 4,5-dihydro-1H-pyrazol-5-yl-substituted 1,2,3-triazoles
    Golovanov, A. A.
    Odin, I. S.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (03) : 447 - 448
  • [32] SYNTHESIS AND ANTIDEPRESSANT PROPERTIES OF NOVEL 2-SUBSTITUTED 4,5-DIHYDRO-1H-IMIDAZOLE DERIVATIVES
    WENTLAND, MP
    BAILEY, DM
    ALEXANDER, EJ
    CASTALDI, MJ
    FERRARI, RA
    HAUBRICH, DR
    LUTTINGER, DA
    PERRONE, MH
    JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (08) : 1482 - 1489
  • [33] Synthesis of 3-substituted pyrazoles by oxidative dehydrogenation of 4,5-dihydro-3H-pyrazoles
    Yakovlev, K. V.
    Petrov, D. V.
    Dokichev, V. A.
    Tomilov, Yu. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (06) : 950 - 952
  • [34] Synthesis of 3-substituted pyrazoles by oxidative dehydrogenation of 4,5-dihydro-3H-pyrazoles
    V. Yakovlev
    D. V. Petrov
    V. A. Dokichev
    Yu. V. Tomilov
    Russian Journal of Organic Chemistry, 2009, 45 : 950 - 952
  • [35] Synthesis of spiro[imidazole-2,2'-pyrroles] by reaction of 4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates with urea
    Dubovtsev, A. Yu.
    Silaichev, P. S.
    Zheleznova, M. A.
    Aliev, Z. G.
    Maslivets, A. N.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (12) : 1779 - 1783
  • [36] Synthesis of spiro[imidazole-2,2′-pyrroles] by reaction of 4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates with urea
    A. Yu. Dubovtsev
    P. S. Silaichev
    M. A. Zheleznova
    Z. G. Aliev
    A. N. Maslivets
    Russian Journal of Organic Chemistry, 2016, 52 : 1779 - 1783
  • [37] Synthesis and Antibacterial Activity of 2-(4,5-Dihydro-3-substituted-1H-pyrazol-5-yl)-3-methoxyquinoxalines
    Devi, T. Rajani
    Laxminarayana, E.
    Giri, T.
    Chary, M. Thirumala
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 30 (03) : 381 - 385
  • [38] SYNTHESIS AND STRUCTURE OF 1-SUBSTITUTED 1-OXO-1,2-DIHYDRO-4H-3,1-BENZOXAPHOSPHORINS
    BOVIN, AN
    CHEKHLOV, AN
    TSVETKOV, EN
    BULLETIN OF THE RUSSIAN ACADEMY OF SCIENCES-DIVISION OF CHEMICAL SCIENCE, 1992, 41 (09): : 1704 - 1708
  • [39] SPIRO(2H-DIBENZO[F,H]-3,4-DIHYDRO-1,5-DIOXACYCLONONENE-3,1'-CYCLOPROPANE)
    KARLE, IL
    GROCHOWSKI, J
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1979, 35 (MAY): : 1293 - 1295
  • [40] One pot synthesis of novel 1,2-dihydro-5-methyl-spiro[4H-3,1-benzoxazine-2,3′[3H]indol]-4,2′-diones
    Saxena, A
    Goswarni, R
    Khanna, P
    Bhagat, S
    Jain, SC
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2004, 43 (11): : 2381 - 2385