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Synthesis and Some Transformations of 7-(Fur-2-yl)-1-methyl-1H-pyrazolo[4,3-g][1,3]benzothiazole

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Abstract

N-Methylation of 5-nitro-1H-indazole in a KOH–DMSO system resulted in a mixture of 1-methyl-5(6)-nitroindazoles in a ratio of 1: 2. Reduction of the isomers with tin in concentrated hydrochloric acid afforded pure 1-methyl-1H-indazole-6-amine. Condensation of the latter with furoyl chloride in 2-propanol yielded N-(1-methylindazol-6-yl)furan-2-carboxamide, treatment of which with an excess of P2S5 in anhydrous pyridine gave the corresponding carbothioamide. 7-(Fur-2-yl)-1-methyl-1H-pyrazolo[4,3-g][1,3]benzothiazole was synthesized by Jacobson oxidation of N-(1-methylindazol-6-yl) furan-2-carbothioamide with potassium ferricyanide in an alkaline medium. Some transformations of 7-(fur-2-yl)-1-methyl-1H-pyrazolo[4,3-g][1,3]- benzothiazole such as formylation and acylation were performed.

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References

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Correspondence to M. M. El’chaninov.

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Original Russian Text © M.M. El’chaninov, A.A. Aleksandrov, V.F. Stepanov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 3, pp. 397–401.

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El’chaninov, M.M., Aleksandrov, A.A. & Stepanov, V.F. Synthesis and Some Transformations of 7-(Fur-2-yl)-1-methyl-1H-pyrazolo[4,3-g][1,3]benzothiazole. Russ J Gen Chem 88, 425–429 (2018). https://doi.org/10.1134/S1070363218030088

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