Interaction of benzimidazole-2-thione with propargyl bromide and 1,3-dibromopropyne

被引：0
|
作者：
T. I. Yaroshenko
A. S. Nakhmanovich
L. I. Larina
V. N. Elokhina
S. V. Amosova
机构：
[1] Siberian Branch of the Russian Academy of Sciences,A. E. Favorsky Irkutsk Institute of Chemistry
来源：
Chemistry of Heterocyclic Compounds | 2008年 / 44卷
关键词：
benzimidazole-2-thione; 2-(3-bromo-2-propynylsulfanyl)-3H-1,3-benzimidazolium bromide; 3-[(; )-bromomethylidene][1,3]thiazolo[3,2-; ][1,3]benzimidazole; 1,3-dibromopropyne; 3-methyl[1,3]thiazolo[3,2-; ][1,3]benzimidazole; 2-(1,2-propadienylsulfanyl)-1H-1,3-benzimidazole; propargyl bromide; 2-(2-propynylsulfanyl)-1H-1,3-benzimidazole; 2-(2-propynylsulfanyl)-3H-1,3-benzimidazolium bromide; intramolecular cyclization;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Interaction of benzimidazole-2-thione with propargyl bromide under found conditions permitted the direct synthesis of 2-(2-propynylsulfanyl)-3H-1,3-benzimidazolium bromide, the base 2-(2-propynylsulfanyl)-1H-1,3-benzimidazole, stable crystalline 2-(1,2-propadienylsulfanyl)-1H-1,3-benzimidazole, and 3-methyl[1,3]thiazolo[3,2-a][1,3]benzimidazole. The reaction of benzimidazole-2-thione with 1,3-dibromopropyne in chloroform or absolute methanol gave 2-(3-bromo-2-propynylsulfanyl)-3H-1,3-benzimidazolium bromide, and in absolute methanole in the presence of a twofold excess of sodium methoxide the reaction proceeded stereo-and regioselectively to give 3-[(Z)-bromomethylidene][1,3]thiazolo[3,2-a][1,3]benzimidazole.
引用
收藏
相关论文
共 50 条
  • [1] Interaction of benzimidazole-2-thione with propargyl bromide and 1,3-dibromopropyne
    Yaroshenko, T. I.
    Nakhmanovich, A. S.
    Larina, L. I.
    Elokhina, V. N.
    Amosova, S. V.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (09) : 1129 - 1134
  • [2] Reaction of 1,1-dimethylhydrazones with propargyl bromide and 1,3-dibromopropyne
    Yelokhina, VN
    Nakhmanovich, AS
    Karnaukhova, RV
    Larina, LI
    Lopyrev, VA
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 36 (04) : 479 - 481
  • [3] Products of reaction of 1,1-dimethylhydrazine with propargyl bromide and 1,3-dibromopropyne
    Elokhina, VN
    Larina, LI
    Nakhmanovich, AS
    Lopyrev, VA
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2000, 70 (11) : 1752 - 1754
  • [4] Thiophene-2-carbaldehyde and benzaldehyde thiosemicarbazones in reactions with propargyl bromide and 1,3-dibromopropyne
    Elokhina, V. N.
    Nakhmanovich, A. S.
    Larina, L. I.
    Yaroshenko, T. I.
    Amosova, S. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (02) : 226 - 228
  • [5] Quinoxaline-2,3-dithiol in reactions with propargyl bromide and 1,3-dibromopropyne
    Yaroshenko, T. I.
    Elokhina, V. N.
    Nakhmanovich, A. S.
    Larina, L. I.
    Komarova, T. N.
    Amosova, S. V.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2009, 79 (06) : 1197 - 1200
  • [6] Thiophene-2-carbaldehyde and benzaldehyde thiosemicarbazones in reactions with propargyl bromide and 1,3-dibromopropyne
    V. N. Elokhina
    A. S. Nakhmanovich
    L. I. Larina
    T. I. Yaroshenko
    S. V. Amosova
    Russian Journal of Organic Chemistry, 2009, 45 : 226 - 228
  • [7] Quinoxaline-2,3-dithiol in reactions with propargyl bromide and 1,3-dibromopropyne
    T. I. Yaroshenko
    V. N. Elokhina
    A. S. Nakhmanovich
    L. I. Larina
    T. N. Komarova
    S. V. Amosova
    Russian Journal of General Chemistry, 2009, 79 : 1197 - 1200
  • [8] Reaction of thiosemicarbazide with 1,3-dibromopropyne
    Volkova, K. A.
    Nakhmanovich, A. S.
    Amosova, S. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (09) : 1379 - 1381
  • [9] Reaction of thiosemicarbazide with 1,3-dibromopropyne
    K. A. Volkova
    A. S. Nakhmanovich
    S. V. Amosova
    Russian Journal of Organic Chemistry, 2007, 43 : 1379 - 1381
  • [10] Alkylation and Aminomethylation of 1,3-Dihydro-2Н-Benzimidazole-2-Thione
    A. Ya. Bespalov
    T. L. Gorchakova
    A. Yu. Ivanov
    M. A. Kuznetsov
    L. M. Kuznetsova
    A. S. Pankova
    L. I. Prokopenko
    M. S. Avdontceva
    Chemistry of Heterocyclic Compounds, 2015, 50 : 1547 - 1558
12345