Ambident polyfluoroalkyl-substituted pyrazoles in the methylation reactions / Ivanova Anna E.,Burgart Yanina V.,Saloutin Viktor I.,Slepukhin Pavel A.,Borisevich Sophia S.,Khursan Sergey L. // JOURNAL OF FLUORINE CHEMISTRY. - 2017. - V. 195, l. . - P. 47-56.

ISSN/EISSN:

0022-1139 / 1873-3328

Type:

Article

Abstract:

The reactivity of polyfluoroallcyl-containing pyrazoles has been estimated using the quantum chemical calculations. A good regioselectivity in the methylation of polyfluoroalkylpyrazoles was reached while varying the reaction conditions. Under basic conditions, methylation of such pyrazoles led to the preferred formation of 3-R-F-pyrazoles, whereas the use of dimethyl sulfate in the absence of a base resulted in the predominant formation of 5-R-F-pyrazoles. A proposed mechanism of methylation was discussed. (C) 2017 Elsevier B.V. All rights reserved.

Author keywords:

Polyfluoroalkylpyrazoles; Ambident nucleophiles; Methylation; Regioselectivity; DFT-study REGIOSELECTIVE SYNTHESIS; ANTIINFLAMMATORY AGENTS; ANTIBACTERIAL ACTIVITY; BIOLOGICAL EVALUATION; DERIVATIVES; 3-TRIFLUOROMETHYLPYRAZOLES; INHIBITORS; CHEMISTRY; CELECOXIB; ANALOGS

DOI:

10.1016/j.jfluchem.2017.01.009

Web of Science ID:

ISI:000395605000007

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAR
Publisher	ELSEVIER SCIENCE SA
Address	PO BOX 564, 1001 LAUSANNE, SWITZERLAND
Language	English
EISSN	1873-3328
Keywords-Plus	REGIOSELECTIVE SYNTHESIS; ANTIINFLAMMATORY AGENTS; ANTIBACTERIAL ACTIVITY; BIOLOGICAL EVALUATION; DERIVATIVES; 3-TRIFLUOROMETHYLPYRAZOLES; INHIBITORS; CHEMISTRY; CELECOXIB; ANALOGS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Inorganic \& Nuclear; Chemistry, Organic
Author-Email	ivanova@ios.uran.ru
ResearcherID-Numbers	Burgart, Yanina/T-8025-2017
ORCID-Numbers	Burgart, Yanina/0000-0001-6061-2410 Khursan, Sergey/0000-0003-1879-944X
Funding-Acknowledgement	Russian Science Foundation {[}16-13-10255]
Funding-Text	This work was financially supported by the Russian Science Foundation (grant 16-13-10255).
Number-of-Cited-References	51
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	3
Journal-ISO	J. Fluor. Chem.
Doc-Delivery-Number	EM9BD