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

Dürüst, Yasar, Karakus, Hamza, Kariuki, Benson M. ORCID: https://orcid.org/0000-0002-8658-3897 and Knight, David W. 2018. Some reactions of 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido) acetic acids. Synthetic Communications 48 (17) , pp. 2206-2220. 10.1080/00397911.2018.1489966

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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
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:	16 Nov 2024 01:15
URI:	https://orca.cardiff.ac.uk/id/eprint/115387

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