Fluoroaryl containing beta,beta `-dioxoesters in the synthesis of fluorobenzopyran-4(2)-ones / Kisil SP,Burgart YV,Saloutin VI,Chupakhin ON // JOURNAL OF FLUORINE CHEMISTRY. - 2001. - V. 108, l. 2. - P. 125-131.

ISSN/EISSN:

0022-1139 / нет данных

Type:

Article

Abstract:

Fluoroaryl containing beta, beta'-dioxoesters and their copper(II) chelates have been prepared by acylation of ethyl acetoacetate with 2,6-dimethoxy-3,4,5-trifluorobenzoyl, 2-methoxy-3,4,5,6-tetrafluorobenzoyl and pentafluorobenzoyl chlorides. Cyclization of these beta,beta'-dioxoesters leads to formation of substituted fluorochromones. Depending on conditions, 2-methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzed to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. The same chromone reacts with morpholine to form a seven-substituted product and ammonium hydroxide to give 3-iminoacetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter affords 3-acetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin Ethyl-2-(2,6-dimethoxy-3,4,5-trifluorobenzoyl)-3-oxobutanoates undergoes ketone-splitting to 1-(2,6-dimethoxy-3,4,5-trifluorophenyl)-1.3-butandione. (C) 2001 Elsevier Science B.V. All rights reserved.

Author keywords:

acylation; beta,beta `-dioxoesters; copper(II) chelate; trifluorochromone; trifluorocoumarin

DOI:

10.1016/S0022-1139(01)00346-3

Web of Science ID:

ISI:000168879700002

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAY
Publisher	ELSEVIER SCIENCE SA
Address	PO BOX 564, 1001 LAUSANNE, SWITZERLAND
Language	English
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Inorganic \& Nuclear; Chemistry, Organic
ResearcherID-Numbers	Burgart, Yanina/T-8025-2017
ORCID-Numbers	Burgart, Yanina/0000-0001-6061-2410
Number-of-Cited-References	7
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	5
Journal-ISO	J. Fluor. Chem.
Doc-Delivery-Number	435KB