The synthesis of 3-(het)aryl-6,7-dihydro-5H-[1,2,4]-triazolo[3,4-a][2]benzazepines

被引:0
|
作者
Vladimir А. Glushkov
Dmitry N. Babentsev
Maksim V. Dmitriev
Kseniya А. Stepanova
Anastasiya Yu. Kharintseva
Anastasiya E. Simakhina
机构
[1] Ural Branch of the Russian Academy of Sciences,Institute of Technical Chemistry
[2] Perm State University,undefined
来源
关键词
4-aryl-2-methylbutan-2-ols; benz[; ]azepines; hetarenecarboxylic acid hydrazides; methyl thiocyanate; 1,2,4-triazolo-2-benzazepines; Ritter reaction;
D O I
暂无
中图分类号
学科分类号
摘要
4-Aryl-2-methylbutan-2-ols with methoxy or methylenedioxy substituents participate in the Graf–Ritter reaction with methyl thiocyanate in the presence of an acid (H2SO4, MeSO3H) forming 1-methylsulfanyl-2-benzazepines in low yields (11–35%), which undergo cyclization with benzhydrazide or hetarenecarboxylic acid hydrazides upon reflux in o-dichlorobenzene into the corresponding 3-phenyl- and 3-hetaryl-6,7-dihydro-5H-1,2,4-triazolo[3,4-a][2]benzazepines (45–74% yields).
引用
收藏
页码:63 / 68
页数:5
相关论文
共 50 条
  • [1] The synthesis of 3-(het)aryl-6,7-dihydro-5H-[1,2,4]-triazolo[3,4-a][2]benzazepines
    Glushkov, Vladimir A.
    Babentsev, Dmitry N.
    Dmitriev, Maksim V.
    Stepanova, Kseniya A.
    Kharintseva, Anastasiya Yu.
    Simakhina, Anastasiya E.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (01) : 63 - 68
  • [2] Synthesis and opening of the thiadiazine ring in 6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines
    Kolodina, A. A.
    Gaponenko, N. I.
    Lesin, A. V.
    RUSSIAN CHEMICAL BULLETIN, 2008, 57 (06) : 1273 - 1276
  • [3] Synthesis and opening of the thiadiazine ring in 6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines
    A. A. Kolodina
    N. I. Gaponenko
    A. V. Lesin
    Russian Chemical Bulletin, 2008, 57 : 1273 - 1276
  • [4] Synthesis of derivatives of 6-aryl-3-methyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-7-carboxylic acid
    Yanchenko, VA
    Malyshev, VV
    Demchenko, AM
    Lozinskii, MO
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2003, (04): : 631 - 633
  • [5] New Synthesis of Derivatives of 6-Aryl-3-methyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-7-carboxylic Acid
    V. A. Yanchenko
    V. V. Malyshev
    A. M. Demchenko
    M. O. Lozinskii
    Chemistry of Heterocyclic Compounds, 2003, 39 (4) : 547 - 548
  • [6] Discovery of ( ±)-3-(1H-pyrazol-1-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazine derivatives with promising in vitro anticoronavirus and antitumoral activity
    Jilloju, Parameshwara Chary
    Persoons, Leentje
    Kurapati, Sathish Kumar
    Schols, Dominique
    De Jonghe, Steven
    Daelemans, Dirk
    Vedula, Rajeswar Rao
    MOLECULAR DIVERSITY, 2022, 26 (03) : 1357 - 1371
  • [7] THE SYNTHESIS OF 3-(ALDITOL-1-YL)-1,2,4-TRIAZOLO[3,4-A]PHTHALAZINES
    SHABAN, MAE
    ALI, RS
    ELBADRY, SM
    CARBOHYDRATE RESEARCH, 1981, 95 (01) : 51 - 60
  • [8] BENZODIAZEPINE RECEPTOR LIGANDS - SYNTHESIS AND PRELIMINARY PHARMACOLOGICAL EVALUATION OF SOME 3-ARYL-6-THIOALKYL-1,2,4-TRIAZOLO[3,4-A]PHTHALAZINES, 3-ARYL-6-ALKYLSULPHINYL-1,2,4-TRIAZOLO[3,4-A]PHTHALAZINES, 3-ARYL-6-ALKYLSULPHONYL-1,2,4-TRIAZOLO[3,4-A]PHTHALAZINES, AND 3-ARYL-6-ALKOXY-1,2,4-TRIAZOLO[3,4-A]PHTHALAZINES
    TARZIA, G
    OCCELLI, E
    CORSICO, N
    LUZZANI, F
    BARONE, D
    FARMACO-EDIZIONE SCIENTIFICA, 1988, 43 (02): : 189 - 201
  • [9] Discovery of ( ±)-3-(1H-pyrazol-1-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazine derivatives with promising in vitro anticoronavirus and antitumoral activity
    Parameshwara Chary Jilloju
    Leentje Persoons
    Sathish Kumar Kurapati
    Dominique Schols
    Steven De Jonghe
    Dirk Daelemans
    Rajeswar Rao Vedula
    Molecular Diversity, 2022, 26 : 1357 - 1371
  • [10] STEREOSPECIFIC SYNTHESIS OF 6,7-DIHYDRO-5H-1,2,4-TRIAZOLO[3,4-B][1,3,4]THIADIAZINES
    IBRAHIM, YA
    ELWAHY, AHM
    ELFIKY, AEM
    HETEROATOM CHEMISTRY, 1994, 5 (04) : 321 - 325