Synthesis and Reactivity of Fusion Product of 2-Methylthiazole Fragment to 2-(Furan-2-yl)benzimidazole
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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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- 3.Pozharskii, A.F., Soldatenkov, A.T., and Katritzky, A.R., Heterocycles in Life and Society, Chichester: J.Wiley & Sons, 1997.Google Scholar
- 4.Fărcăşan, V. and Makkay, C., Acad. Rep. Populare Române, Filiala Cluj, St. Cerc. Chim., 1959, vol. 10, p.145.Google Scholar
- 6.Weidenhagen, R., Ber., 1936, vol. 69, p. 2263.Google Scholar
- 7.Elchaninov, M.M., Achkasova, A.A., Aleksandrov, А.А., and Luk’yanov, B.S., RF Patent no. 2237667, 2002; Byull. Izobret., 2004, no.28.Google Scholar