SYNTHESIS OF 1,2,4-TRIAZOLO[4,3-D][1,4]DIAZEPINES AND 1,2,4-OXADIAZOLO[4,5-D][1,4]DIAZEPINES BY 1,3-DIPOLAR CYCLOADDITION

被引:32
|
作者
HASNAOUI, A [1 ]
BAOUID, A [1 ]
LAVERGNE, JP [1 ]
机构
[1] UNIV MONTPELLIER 2,SYNTH & ETUD PHYSICOCHIM LAB,CNRS,UA 468,F-34095 MONTPELLIER 2,FRANCE
关键词
D O I
10.1002/jhet.5570280113
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report here a one-step synthesis of the 4,5,6,7-tetrahydro-lH-1,2,4-triazolo[4,3-dI1,4]diazepine, 4-6, and 1,2,4-oxadiazolo[4,5-dIl,4]-diazepine, 7-10, by 1,3-dipolar cycloaddition of nitrile imines and nitrile oxides with 2,3-dihydro-1H-1,4-diazepine, 1. In all cases these cycloadditions are peri- and regioselectives (the C = N bond is sole affected) and occurs with high yields. Structure and conformations of cycloadducts have been assigned by means of nmr analysis.
引用
收藏
页码:73 / 76
页数:4
相关论文
共 50 条
  • [21] Synthesis of 2-methyl-1,2,4-triazolo[4,3-d]-1,2,4-triazino[2,3-a]-benzimidazole and 2-methyl-9-phenylimidazo[1,2-b]-1,2,4-triazolo[4,3-d]-1,2,4-triazine
    V. P. Kruglenko
    V. P. Gnidets
    M. V. Povstyanoi
    Chemistry of Heterocyclic Compounds, 2000, 36 (1) : 103 - 104
  • [22] Synthesis of substituted imidazo[1,2-b]-1,2,4-triazolo[4,3-d]-1,2,4-triazepine and 4H-imidazo[1,2-b]-1,2,4-triazino[4,3-d]-1,2,4-triazepin-7-one
    Kruglenko, VP
    Povstyanoy, MV
    Klyuev, NA
    Idzikovsky, VA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1997, (10): : 1420 - 1421
  • [24] Synthesis of substituted imidazo[1,2-b]-1,2,4-triazolo[4,3-d]-1,2,4-triazepine and 4H-imidazo[1,2-b]-1,2,4-triazino[4,3-d]-1,2,4-triazepin-7-one
    Kruglenko V.P.
    Povstyanoi M.V.
    Klyuev N.A.
    Idzikovskii V.A.
    Chemistry of Heterocyclic Compounds, 1997, 33 (10) : 1238 - 1239
  • [25] SYNTHESIS OF 5-ARYL-1-METHYL-[1,2,4]-TRIAZOLO[4,3-D] TETRAZOLES
    SCOTT, FL
    BUTLER, RN
    CRONIN, DA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1965, 4 (11) : 950 - &
  • [26] Synthesis and evaluation of the anticonvulsant activity of 8-alkoxy-4,5-dihydrobenzo[b][1,2,4]triazolo[4,3-d][1,4]thiazepine derivatives
    Deng, Xian-Qing
    Song, Ming-Xia
    Wang, Shi-Ben
    Quan, Zhe-Shan
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2014, 29 (02) : 272 - 280
  • [27] Syntheses of Potentially Bioactive [1,2,4]Oxadiazolo[5,4-d]benzothiazepines by 1,3-Dipolar Cycloaddition
    Wu, Xiao-Long
    Liu, Fang-Ming
    Shen, Song-Wei
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (06) : 1350 - 1355
  • [28] Synthesis and structure characterization of new 1,2,4-oxadiazolo[4,5-d]-1,5-benzothiazepines derivatives containing 2-phenyl-1,2,3-triazole through 1,3-dipolar cycloaddition reaction
    Yang, De-Bao
    Liu, Fang-Ming
    Xu, Feng
    Yang, Chun
    Ye, Jia-Wei
    Shen, Song-Wei
    Zhou, Ying-Lei
    Li, Wei
    MOLECULAR DIVERSITY, 2008, 12 (02) : 103 - 109
  • [29] Synthesis and structure characterization of new 1,2,4-oxadiazolo[4,5-d]-1,5-benzothiazepines derivatives containing 2-phenyl-1,2,3-triazole through 1,3-dipolar cycloaddition reaction
    De-Bao Yang
    Fang-Ming Liu
    Feng Xu
    Chun Yang
    Jia-Wei Ye
    Song-Wei Shen
    Ying-Lei Zhou
    Wei Li
    Molecular Diversity, 2008, 12
  • [30] Synthesis of new [1,2,4]triazolo and [1,2,4]oxadiazolo-[1,3,4]benzotriazepines
    El Messaoudi, T
    El Messaoudi, M
    Zair, T
    Hasnaoui, A
    Esseffar, M
    Lavergne, JP
    SYNTHETIC COMMUNICATIONS, 2002, 32 (12) : 1815 - 1820