Synthesis of polyfluorinated arylhydrazines, arylhydrazones and 3-methyl-1-aryl-1H-indazoles

Synthesis of polyfluorinated arylhydrazines, arylhydrazones and 3-methyl-1-aryl-1H-indazoles Научная публикация

Журнал

Journal of Fluorine Chemistry
ISSN: 0022-1139

Вых. Данные

Год: 2018, Том: 214, Страницы: 48-57 Страниц : 10 DOI: 10.1016/j.jfluchem.2018.06.011

Ключевые слова

Polyfluorinated arylhydrazines; p-TSA-induced condensation; C-F activation; Polyfluorinated azaheterocycles; 1H-indazole derivatives; (E)-arylhydrazones

Авторы

Politanskaya Larisa ^1,2 , Bagryanskaya Irina ^1,2 , Tretyakov Evgeny ^1,2

Организации

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Ac Lavrentiev Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 2 Pirogova Str, Novosibirsk 630090, Russia

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.

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

Опубликована в печати:

1 окт. 2018 г.

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