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

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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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Correspondence to M. M. Elchaninov.

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Original Russian Text © M.M. Elchaninov, A.A. Aleksandrov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 8, pp. 1189–1193.

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Elchaninov, M.M., Aleksandrov, A.A. Synthesis and Reactivity of Fusion Product of 2-Methylthiazole Fragment to 2-(Furan-2-yl)benzimidazole. Russ J Org Chem 54, 1200–1204 (2018). https://doi.org/10.1134/S1070428018080134

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  • DOI: https://doi.org/10.1134/S1070428018080134

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