Reactions of 4-hydroxy-5,6,7,8-tetrafluorocoumarin derivatives with S-nucleophiles / Bazyl' IT,Kisil' SP,Burgart YV,Saloutin VI // JOURNAL OF FLUORINE CHEMISTRY. - 2000. - V. 103, l. 1. - P. 3-12.

ISSN/EISSN:

0022-1139 / нет данных

Type:

Article

Abstract:

In the reactions with o-aminothiophenol, 4-hydroxy-(3-(imino)acetyl)-5,6,7,8-tetrafluorocoumarins give products of S-substitution at the C-7 atom. 7-Substituted 5,6,8-trifluorocoumarins form benzothiazole as a result of heterocyclic ring opening; 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorochromone undergoes acid splitting to 2-(2-hydroxy-3,4,5,6-tetrafluorophenyl)benzothiazole. Under alkaline conditions, S-substituted coumarins decompose to acetophenone. In an acid medium, 4-hydroxy-3-iminoacetyl-5,6,8-trifluoro-7-(2-aminophenylthio)coumarin affords 7-(2-aminophenylthio)-2-methyl-5,6,8-trifluorochromone. 4-Hydroxy-5,6-difluoro-2-H-pyrano{[}6,5-a]phenothiazin-2-one was isolated from condensation of 7-(2-aminophenylthio)-4-hydroxy-5,6,8-trifluorocoumarin in the presence of NaH. Reactions of 3-acetyl(iminoacetyl)-4-hydroxy-5,6,7,8-tetrafluorocoumarins and 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorochromone with 2-mercaptoethanol result in the formation of 5,7,8-trisubstituted derivatives. Interaction of 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorochromone with 2-mercaptoethanol, mercaptoacetic acid and 1,2-ethanedithiol leads to the formation of the 7-substituted products. Acyl-lactone rearrangement of mono- and trisubstituted chromones gives the corresponding coumarins. (C) 2000 Elsevier Science S.A. All rights reserved.

Author keywords:

fluorocoumarin; fluorochromone; S-nucleophile; o-aminothiophenol; 2-mercaptoethanol; displacement; opening of cycle; acid splitting; cyclization; acyl-lactone rearrangement N-NUCLEOPHILES; AGENTS

DOI:

10.1016/S0022-1139(99)00210-9

Web of Science ID:

ISI:000086722500002

Соавторы в МНС:

Другие поля

Поле	Значение
Month	APR
Publisher	ELSEVIER SCIENCE SA
Address	PO BOX 564, 1001 LAUSANNE, SWITZERLAND
Language	English
Keywords-Plus	N-NUCLEOPHILES; AGENTS
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	18
Usage-Count-Since-2013	5
Journal-ISO	J. Fluor. Chem.
Doc-Delivery-Number	308PR