TITLE

Features of reactions of polyfluorinated ethyl 4-oxo-2-pnenyl-4 H-chromene-3-carboxylates with N-nucleophiles

AUTHOR(S)
Shcherbakov, K.; Burgart, Ya.; Saloutin, V.
PUB. DATE
May 2013
SOURCE
Russian Journal of Organic Chemistry;May2013, Vol. 49 Issue 5, p719
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
Ethyl 5,6,7,8-tetrafluoro-4-oxo-2-phenyl-4H-chromene-3-carboxylate in reactions with primary amines is characterized by a chromone-coumarin rearrangement affording 3-[amino(phenyl)methylene]-6,7,8-trifluoro-2 H-chromene-2,4(3 H)-diones, and ethyl 4-oxo-2-phenyl-5,6,7,8-tetrafluoro-4 H-chromene-3-carboxylate characteristically adds the amine at the C site of the flavone furnishing 3-amino-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylates which depending on the substituent at the amino group are capable of intramolecular cyclization into 3-[(alkylamino)(phenyl)methylene]-5,6,7,8-tetrafluoro-2 H-chromene-2,4(3 H)-dione or in the case of benzylamine substituent, into ethyl 1-benzyl-5-hydroxy-4-oxo-2-phenyl-6,7,8-trifluoro-1,4-dihydroquinoline-3-carboxylate. The main process in the reaction of tri- and tetrafluoroflavones with secondary amine (1-methylpiperazine) is the nucleophilic substitution at the C of flavone. In the reaction with 1,2-phenylenediamine 3-[(2-aminophenyl)amino]-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylate was obtained from tetrafluoroflavone and 1 H-benzimidazol-2-yl(3,4,5-trifluoro-2-hydroxyphenyl)methanone, from trifluoroflavone.
ACCESSION #
88060426

 

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