SYNTHESIS OF FLUOROALKYLATED DIHYDROAZOLO{[}1,5-a]PYRIMIDINES AND THEIR RING-CHAIN ISOMERISM / Goryaeva Marina V.,Burgart Yanina V.,Saloutin Victor I.,Sadchikova Elena V.,Ulomskii Evgeny N. // HETEROCYCLES. - 2009. - V. 78, l. 2. - P. 435-447.

ISSN/EISSN:

0385-5414 / нет данных

Type:

Article

Abstract:

Cyclisation of ethyl 2-ethoxymethylidene-3-polyfluoroalkyl-3-oxopropionates with 3 -amino-1H-{[}1,2,4]triazole, 3-amino-5-methylpyrazole, ethyl 3-aminopyrazole-4-carboxylate and ethyl 5-aminoimidazole-4-carboxylate hydrochloride results in the formation of polyfluoroalkylated dihydroazolo{[}1,5-a]pyrimidines. The latter are subject to ring-chain isomerisation in solutions depending on the solvent and the ``length{''} of the fluoroalkyl substituent to yield ethyl 3-polyfluoroalkyl-3-oxo-2-{[}(azol-3-yl)aminomethylidene]propionates via opening of the heterocycle at the C-N bond. Dehydration of dihydroazolo{[}1,5-a]pyrimidine were realized.

Author keywords:

Ethyl 2-Ethoxymethylidene-3-polyfluoroalkyl-3-oxopropionate Aminoazole; Cyclization; Dihydroazolo{[}1,5-a]pyrimidine; Ring-Chain Isomerisation

DOI:

10.3987/COM-08-11524

Web of Science ID:

ISI:000263714400013

Соавторы в МНС:

Другие поля

Поле	Значение
Month	FEB 1
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Research-Areas	Chemistry
Web-of-Science-Categories	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	Ural branch of the Russian Academy of Sciences {[}3758.2008.3]
Funding-Text	This study was financially supported by the Grant for young scientists and postgraduates of the Ural branch of the Russian Academy of Sciences for 2008 and by the Program for the support of leading scientific schools (Grant no. 3758.2008.3).
Number-of-Cited-References	15
Usage-Count-Since-2013	2
Journal-ISO	Heterocycles
Doc-Delivery-Number	412GY