Russian Journal of General Chemistry

, Volume 88, Issue 3, pp 425–429 | Cite as

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

  • M. M. El’chaninov
  • A. A. Aleksandrov
  • V. F. Stepanov
Article
  • 13 Downloads

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.

Keywords

5-nitroindazole oxidation 1-methyl-1H-5(6)-nitroindazole potassium ferricyanide electrophilic substitution reactions formylation acylation 

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Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • M. M. El’chaninov
    • 1
  • A. A. Aleksandrov
    • 1
  • V. F. Stepanov
    • 1
  1. 1.Platov South-Russian State Polytechnic University (NPI)NovocherkasskRussia

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