Reactions of 2-Mono- and 2,6-Disubstituted 4-Pyrones with Phenylhydrazine as General Method for the Synthesis of 3-(N-Phenylpyrazolyl)Indoles / Obydennov D. L.,Usachev B. I.,Sosnovskikh V. Ya. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2015. - V. 50, l. 10. - P. 1388-1403.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

Phenylhydrazine reacted regioselectively with 6-substituted 4-pyrone-2-carboxylic acids (or esters) in protic and aprotic solvents, leading to phenylhydrazones of 3-(3-R-1-phenylpyrazol-5-yl)- or 3-(5-R-1-phenylpyrazol-3-yl)pyruvic acids (or esters), respectively. 6-Di(tri)fluoromethylcomanic acids (or esters) reacted analogously, forming the corresponding phenylhydrazones with R-F group in the side chain. The obtained phenylhydrazones underwent Fischer reaction under acidic conditions, forming the respective 3-(N-phenylpyrazolyl)indoles. In contrast to comanic acid and its ester, the reactions of 2-substituted 4-pyrones occurred non-selectively and gave mixtures of regioisomeric pyrazoles with phenylhydrazone group in the side chain or 3-(N-phenylpyrazolyl)indoles. A mechanism was proposed to explain the effect of solvent on the course of reaction.

Author keywords:

comanic acid; indoles; phenylhydrazine; pyrazoles; 4-pyrones; Fischer reaction; regioselectivity 6-(TRIFLUOROMETHYL)COMANIC ACID; BIOLOGICAL EVALUATION; DERIVATIVES; INHIBITORS; HETEROCYCLES; COX-2

DOI:

10.1007/s10593-014-1603-3

Web of Science ID:

ISI:000348348000003

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JAN
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	6-(TRIFLUOROMETHYL)COMANIC ACID; BIOLOGICAL EVALUATION; DERIVATIVES; INHIBITORS; HETEROCYCLES; COX-2
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	dobydennov@mail.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}14-03-31925]; development program at Ural Federal University for the winners of competition ``Young scientists of Ural Federal University{''}
Funding-Text	This work received financial support from the Russian Foundation for Basic Research (project No. 14-03-31925) and the development program at Ural Federal University for the winners of competition ``Young scientists of Ural Federal University{''}.
Number-of-Cited-References	29
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	8
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	AZ6RX