INTERACTION OF BENZIMIDAZOLE-2-THIONE WITH PROPARGYL BROMIDE AND 1,3-DIBROMOPROPYNE

Authors

  • Т. И. Ярошенко A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk 664033
  • А. С. Нахманович A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk 664033
  • Л. И. Ларина A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk 664033
  • В. Н. Елохина A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk 664033
  • С. В. Амосова A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk 664033

DOI:

https://doi.org/10.1007/7206

Keywords:

benzimidazole-2-thione, 2-(3-bromo-2-propynylsulfanyl)-3H-1, 3-benzimidazolium bromide, 3-[(Z)-bromomethylidene][1, 3]thiazolo[3, 2-a][1, 3]benzimidazole, 1, 3-dibromopropyne, 3-methyl-[1, 2-(1, 2-propadienylsulfanyl)-1H-1, 3-benzimidazole, propargyl bromide, 2-(2-propynylsulfanyl)-1H-1, 2-(2-propynylsulfanyl)-3H-1, intramolecular cyclization

Abstract

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-propynyl-sulfanyl)-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)-bromo-methylidene][1,3]thiazolo[3,2-a][1,3]benzimidazole.

How to Cite
Yaroshenko, T. I.; Nakhmanovich, A. S.; Larina, L. I.;
Elokhina, V. N.; Amosova, S. V.  Chem. Heterocycl. Compd. 2008, 44, 1129. [Khim. Geterotsikl. Soedin. 2008, 1399.]

For this article in the English edition see DOI 10.1007/s10593-008-0166-6


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Published

2022-11-24

Issue

No. 9 (2008)

Section

Original Papers