Abstract: 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.

Cite: Politanskaya L. , Bagryanskaya I. , Tretyakov E.
Synthesis of polyfluorinated arylhydrazines, arylhydrazones and 3-methyl-1-aryl-1H-indazoles
Journal of Fluorine Chemistry. 2018. V.214. P.48-57. DOI: 10.1016/j.jfluchem.2018.06.011 WOS Scopus РИНЦ

Dates:

Published print:

Oct 1, 2018

Identifiers:

Web of science	WOS:000446808600008
Scopus	2-s2.0-85051141300
Elibrary	35724707
OpenAlex	W2810277844

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