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;
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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.
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