Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 214, Issue -, Pages 48-57Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2018.06.011
Keywords
Polyfluorinated arylhydrazines; p-TSA-induced condensation; C-F activation; Polyfluorinated azaheterocycles; 1H-indazole derivatives; (E)-arylhydrazones
Categories
Funding
- Russian Ministry of Science and Education under 5-100 Excellence Programme
Ask authors/readers for more resources
Polyfluorinated arylhydrazones were synthesized starting from 1-(4-amino-tetrafluorophenyl)ethanone and polyfluorinated arylhydrazines by action of p-toluenesulfonic acid in good yields. The resulting mixtures of E- and Z-isomers were next treated with K2CO3 in MeCN at room temperature. Under these mild reaction conditions Z-isomers underwent intramolecular nucleophilic cyclization to form 3-methyl-1-aryl-1H-indazole derivatives, while E-isomers were not active and were isolated unchanged. Molecular and crystal structures of prepared polyfluorinated (E)-arylhydrazones as well as selected 3-methyl-1-aryl-1H-indazoles were solved by the X-ray diffraction analysis. Meanwhile, the polyfluorinated acetophenone reacted with hydrazine in THE in the absence of a catalyst through a condensation-nucleophilic substitution cascade process to form a 3-methyl-1H-indazole derivative in excellent yield.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available