Title
Synthesis And Reactions Of 2-Hydroxy-4-Oxo-4-(2,3,5,6-Tetrafluoro-4- Methoxyphenyl)-But-2-Enoic Acid Methyl Ester
Keywords
2-Hydroxy-4-oxo-4-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-but-2-enoic acid methyl ester; 3-(2,3,5,6-Tetrafluoro-4-methoxyphenyl)-propene-1,3-dione; 5-(2,3,5,6-Tetrafluoro-4-methoxyphenyl)-furan-2,3- dione
Abstract
2-Hydroxy-4-oxo-4-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-but-2-enoic acid methyl ester (1) was synthesized by the reaction of pentafluoroacetophenone with dimethyl oxalate in the presence of sodium methylate. Subsequently, reactions of compound 1 with aniline, o-phenylenediamine, and o-aminophenol were investigated. In addition, the thermal cyclization of ester 1 was studied and led to the formation of 5,6,8-trifluoro-7-methoxy-4-oxo-4H-chromene-2-carboxylic acid methyl ester (6) due to nucleophilic substitution of the 3-fluoro group. Hydrolysis of compound 1 and subsequent cyclization by treatment with SOCl2 gave 5-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-furan-2, 3-dione (3). Thermal decarbonylation of compound 3 under mild conditions resulted in the formation of 3-(2,3,5,6-tetrafluoro-4-methoxyphenyl)- propene-1,3-dione (4) which dimerized to pyranone 5. © 2003 Elsevier Science B.V. All rights reserved.
Publication Date
6-1-2003
Publication Title
Journal of Fluorine Chemistry
Volume
121
Issue
2
Number of Pages
201-204
Document Type
Article
Personal Identifier
scopus
DOI Link
https://doi.org/10.1016/S0022-1139(03)00031-9
Copyright Status
Unknown
Socpus ID
0038329196 (Scopus)
Source API URL
https://api.elsevier.com/content/abstract/scopus_id/0038329196
STARS Citation
Pimenova, Elena V.; Krasnych, Olga P.; and Goun, Elena A., "Synthesis And Reactions Of 2-Hydroxy-4-Oxo-4-(2,3,5,6-Tetrafluoro-4- Methoxyphenyl)-But-2-Enoic Acid Methyl Ester" (2003). Scopus Export 2000s. 1733.
https://stars.library.ucf.edu/scopus2000/1733