Synthesis and Reactivity of Fusion Product of 2-Methylthiazole Fragment to 2-(Furan-2-yl)benzimidazole
- Autores: Elchaninov M.M.1, Aleksandrov A.A.1
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Afiliações:
- Platov Southern Russian State Polytechnic University
- Edição: Volume 54, Nº 8 (2018)
- Páginas: 1200-1204
- Seção: Article
- URL: https://journals.rcsi.science/1070-4280/article/view/218601
- DOI: https://doi.org/10.1134/S1070428018080134
- ID: 218601
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Resumo
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.
Sobre autores
M. Elchaninov
Platov Southern Russian State Polytechnic University
Autor responsável pela correspondência
Email: elchaninov22@gmail.com
Rússia, ul. Prosveshcheniya 132, Novocherkassk, 346428
A. Aleksandrov
Platov Southern Russian State Polytechnic University
Email: elchaninov22@gmail.com
Rússia, ul. Prosveshcheniya 132, Novocherkassk, 346428
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