New fluoroaryl-containing beta,beta `-dioxoesters in the synthesis of fluorobenzopyran-2(4)-ones / Kisil' SP,Burgart YV,Saloutin VI // RUSSIAN JOURNAL OF ORGANIC CHEMISTRY. - 2001. - V. 37, l. 10. - P. 1455-1462.

ISSN/EISSN:

1070-4280 / нет данных

Type:

Article

Abstract:

For the first time were obtained ethyl 2-(2-methoxy-3,4,5,6-tetrafluorobenzoyl)-3-oxobutanoate and ethyl 2-pentafluorobenzoyl-3-oxobutanoate and their copper chelates. The compounds were prepared by acylation of ethyl acetoacetate with 2-methoxy-3,4,5,6-tetrafluoro- and pentafluorobenzoyl chlorides. Cyclization of these beta,beta(1)-dioxoesters afforded substituted chromones. 2-Methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzes depending on reaction conditions either to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or to 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. Reaction with morpholine provided 7-substituted product, and with aqueous ammonia as a result of rearrangement forms 3-acetimidoyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter yields 3-acetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin.

Author keywords:

SELECTIVE ORTHO-METHOXYLATION; N-NUCLEOPHILES; DERIVATIVES

DOI:

10.1023/A:1013479323203

Web of Science ID:

ISI:000173862000011

Соавторы в МНС:

Другие поля

Поле	Значение
Month	OCT
Publisher	MAIK NAUKA/INTERPERIODICA
Address	C/O KLUWER ACADEMIC-PLENUM PUBLISHERS, 233 SPRING ST, NEW YORK, NY 10013-1578 USA
Language	English
Keywords-Plus	SELECTIVE ORTHO-METHOXYLATION; N-NUCLEOPHILES; DERIVATIVES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
ResearcherID-Numbers	Burgart, Yanina/T-8025-2017
ORCID-Numbers	Burgart, Yanina/0000-0001-6061-2410
Number-of-Cited-References	15
Usage-Count-Since-2013	1
Journal-ISO	Russ. J. Organ. Chem.
Doc-Delivery-Number	521VL