Fluorine-containing 3-arylhydrazono-2,4-dioxobutanoates in reactions with difunctional nucleophiles / Fokin A. S.,Burgart Ya. V.,Saloutin V. I. // RUSSIAN JOURNAL OF ORGANIC CHEMISTRY. - 2006. - V. 42, l. 6. - P. 887-896.

ISSN/EISSN:

1070-4280 / нет данных

Type:

Article

Abstract:

3-Arylhydrazono-4-polyfluoroalkyl-2,4-dioxobutanoates reacted with hydrazines to give ethyl 4-aryldiazeno-3-polyfluoroalkyl-1H-pyrazole-5-carboxylates, while analogous reactions of ethyl 3-arylhydrazono-4-pentafluorophenyl-2,4-dioxobutanoates resulted in the formation of 4-aryldiazeno-3-pentafluorophenyl-1,2-dihydropyridazine-5,6-diones or 6-aryl-7,8,9,10-tetrafluoro-2-phenyl-2,4a,6,10b-tetradropyridazo{[}4,3-c ]cinnoline-3.4-diones, depending on the conditions. Cyclocondensation of ethyl 3-arylhydrazono-4-polyfluoroalkyl(or pentafluorophenyl)-2,4-dioxobutanoates with ethylenediamine led to 3-{[}1-arylhydrazono-2-oxo-2-polyfluoroalkyl(or pentafluorophenyl)ethyl]-5,6-dihydropyrazin-2(IH)-ones, and 3-{[}1-arylhydrazono-2-oxo-2-polyfluoroalk-yl(pentafluorophenyl)ethyl]be nzoxazin-2-ones were formed in the condensation with o-aminophenol. Pentafluorophenyl-substituted heterocycles were found to undergo intramolecular ring closure to give 3-hetarylsubstituted 1-aryl-5,6,7,8-tetrafluoro-1,4-dihydrocinnolin-4-ones. The reactions of ethyl 3-arylhydrazono-4-pentafluorophenyl-2,4-dioxobutanoates with o-aminobenzenethiol gave 3-{[}7-(2-aminophenylsulfanyl)1-aryl-5,6,8-trifluoro-4-oxo-1,4-dihydroci nnolin-3-yl]benzothiazin-2-ones; 8a-hydroxy-11,12,13,14-tetrafluoro-10(4-methoxyphenyl)-2,3,4,5,6,7,8a, I 0-octahydropyrazino {[} 1', 2': 4,5] {[}1,4] diazepino {[}6,7-c] cinnolin- 8 -one was isolated in the condensation of ethyl 3-(4-methoxyphenylhydrazono)-4-pentafluorophenyl-2,4-dioxobutanoate with N-(2-aminoethyl)ethane-1,2-diamine.

Author keywords:

HETEROCYCLIZATION

DOI:

10.1134/S1070428006060133

Web of Science ID:

ISI:000239375600013

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUN
Publisher	MAIK NAUKA/INTERPERIODICA/SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013-1578 USA
Language	English
Keywords-Plus	HETEROCYCLIZATION
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	saloutin@ios.uran.ru
ResearcherID-Numbers	Burgart, Yanina/T-8025-2017
ORCID-Numbers	Burgart, Yanina/0000-0001-6061-2410
Number-of-Cited-References	10
Usage-Count-Since-2013	1
Journal-ISO	Russ. J. Organ. Chem.
Doc-Delivery-Number	068LN