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Russian Journal of Organic Chemistry

, Volume 54, Issue 8, pp 1200–1204 | Cite as

Synthesis and Reactivity of Fusion Product of 2-Methylthiazole Fragment to 2-(Furan-2-yl)benzimidazole

  • M. M. Elchaninov
  • A. A. Aleksandrov
Article
  • 6 Downloads

Abstract

Reaction of 1,2-diamino-4-nitrobenzene with furan-2-carbaldehyde in the presence of copper sulfate afforded 2-(furan-2-yl)-5(6)-nitro-1H-benzimidazole. Its N-methylation provided 1-methyl-5(6)-nitro isomers. After reduction of isomers with tin in conc. HCl a pure 3-methyl-2-(furan-2-yl)benzimidazol-5-amine was obtained. The condensation of this amine with acetic anhydride led to the formation of N-[3-methyl-2-(furan-2-yl)benzimidazol-5-yl]acetamide whose treatment with excess P2S5 in anhydrous pyridine resulted in the corresponding thioamide. The latter was oxidized with K3[Fe(CN)6] in alkaline environment to obtain 2,8-dimethyl-7-(furan-2-yl)-8H-imidazo[4,5-g][1,3]benzothiazole. Its reactions of electrophilic substitution were studied: nitration, bromination, sulfonation, formylation, acylation. The substituent is introduced exclusively in the position 5 of the furan ring.

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Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  1. 1.Platov Southern Russian State Polytechnic UniversityNovocherkasskRussia

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