Some reactions of 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido) acetic acids

In situ generated 2,4-diaryl substituted münchnones from 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido)acetic acids react with acetic anhydride in the presence of 2-nitromethylene thiazolidine, which is most likely acting as a base, and unexpectedly undergo a Dakin-West type reaction...

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Bibliographic Details
Published in:Synthetic communications 2018-09, Vol.48 (17), p.2206-2220
Main Authors: Dürüst, Yaşar, Karakuş, Hamza, Kariuki, Benson M., Knight, David W.
Format: Article
Language:English
Subjects:
Acids
Acyl urea
Anhydrides
Autoxidation
Benzoic acid
Carbodiimides
Dakin-West reaction
Infrared spectroscopy
Münchnone precursor
nitromethylene thiazolidine
NMR
Nuclear magnetic resonance
Substitutes
X-ray diffraction
Yogurt
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Summary:In situ generated 2,4-diaryl substituted münchnones from 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido)acetic acids react with acetic anhydride in the presence of 2-nitromethylene thiazolidine, which is most likely acting as a base, and unexpectedly undergo a Dakin-West type reaction and a concurrent autoxidation reaction leading to the formation of (E)-1-(N,4-dimethylbenzamido)-1-(4-fluorophenyl)prop-1-en-2-yl acetate, 4-substitutedphenyl-N-methyl-N-(4-substitutedbenzoyl) benzamides and p-substituted benzoic acids. In addition, a novel and efficient access to N-acyl urea derivatives is described by the reaction between 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido)acetic acids and cyclohexyl, isopropyl carbodiimides in the presence of a base. The structures of all new products were identified on the basis of NMR and IR spectra, along with X-ray diffraction data and HRMS measurements.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2018.1489966