Abstract
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.
Item Type: |
Article
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Date Type: |
Published Online |
Status: |
Published |
Schools: |
Chemistry |
Publisher: |
Taylor & Francis: STM, Behavioural Science and Public Health Titles |
ISSN: |
0039-7911 |
Date of First Compliant Deposit: |
1 October 2018 |
Date of Acceptance: |
9 July 2018 |
Last Modified: |
19 Oct 2019 23:09 |
URI: |
http://orca-mwe.cf.ac.uk/id/eprint/115387 |
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