Peculiarities of cyclization of ethyl 2-ethoxymethylene-3-oxo-3-(polyfluoroalkyl)propionates with 3-amino-5-hydroxypyrazole / Goryaeva Marina V.,Burgart Yanina V.,Saloutin Viktor I. // JOURNAL OF FLUORINE CHEMISTRY. - 2013. - V. 147, l. . - P. 15-21.

ISSN/EISSN:

0022-1139 / нет данных

Type:

Article

Abstract:

The reactions of ethyl 2-ethoxymethylene-3-oxo-3-(polyfluoroalkyl)propionates with 3-amino-5-hydroxypyrazole result in ethyl 2,7-dihydroxy-7-(polyfluoroalkyl)-4,7-dihydropyrazolo{[}1,5-a]pyrimidin- 6-carboxylates under mild conditions. These products undergo recyclization in refluxing ethanol to form ethyl 3-hydroxy-4-(polyfluoroalkyl)-1H-pyrazolo{[}3,4-b]pyridin-5-carboxylates , whereas in refluxing glacial acetic acid they are dehydrated to ethyl 2-hydroxy-7-(polyfluoroalkyl)pyrazolo{[}1,5-a]pyrimidin-6-carboxylates. The non-fluorinated ethyl 2-ethoxymethylene-3-oxo esters in the reactions with 3-amino-5-hydroxypyrazole in ethanol (or glacial acetic acid) under reflux form only ethyl 2-hydroxy-7-phenyl(hydroxy)pyrazolo{[}1,5-c]pyrimidin-6-carboxylates. (C) 2013 Elsevier B.V. All rights reserved.

Author keywords:

Ethyl 2-ethoxymethylene-3-oxo-3-(polyfluoroalkyl)propionates; 3-Amino-5-hydroxypyrazole; Pyrazolo{[}1,5-a]pyrimidines; Pyrazolo{[}3,4-b]pyridines; Recyclization RING-CHAIN ISOMERISM; ANTIPROLIFERATIVE AGENTS; BIOLOGICAL EVALUATION; PHENYL AMIDES; INHIBITORS; DERIVATIVES; POTENT; PYRAZOLO<1,5-A>PYRIMIDINES; PYRAZOLOPYRIDINES; IDENTIFICATION

DOI:

10.1016/j.jfluchem.2013.01.005

Web of Science ID:

ISI:000316710000004

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAR
Publisher	ELSEVIER SCIENCE SA
Address	PO BOX 564, 1001 LAUSANNE, SWITZERLAND
Language	English
Keywords-Plus	RING-CHAIN ISOMERISM; ANTIPROLIFERATIVE AGENTS; BIOLOGICAL EVALUATION; PHENYL AMIDES; INHIBITORS; DERIVATIVES; POTENT; PYRAZOLO<1,5-A>PYRIMIDINES; PYRAZOLOPYRIDINES; IDENTIFICATION
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Inorganic \& Nuclear; Chemistry, Organic
Author-Email	pmv@ios.uran.ru
ResearcherID-Numbers	Burgart, Yanina/T-8025-2017
ORCID-Numbers	Burgart, Yanina/0000-0001-6061-2410
Funding-Acknowledgement	Ministry of Education and Science of the Russian Federation {[}8430]; Ural Branch of RAS {[}12-P-3-1030]; State Program for Supporting of Leading Scientific Schools of the Russian Federation {[}5505.2012.3]; Russian Foundation for Basic Research {[}13-03-00617]
Funding-Text	This research was financially supported by the Ministry of Education and Science of the Russian Federation (Project 8430), the Program of the Ural Branch of RAS (Project 12-P-3-1030), the State Program for Supporting of Leading Scientific Schools of the Russian Federation (Grant 5505.2012.3) and the Russian Foundation for Basic Research (Grant 13-03-00617).
Number-of-Cited-References	41
Usage-Count-Since-2013	2
Journal-ISO	J. Fluor. Chem.
Doc-Delivery-Number	113ZU