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

N -Methylation of 5-nitro-1 H -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-1 H -indazole-6-amine. Condensation of the latter with furoyl chloride in...

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Veröffentlicht in:Russian journal of general chemistry 2018-03, Vol.88 (3), p.425-429
Hauptverfasser: El’chaninov, M. M., Aleksandrov, A. A., Stepanov, V. F.
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Sprache:eng
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Zusammenfassung:N -Methylation of 5-nitro-1 H -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-1 H -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.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363218030088