Cardiff University | Prifysgol Caerdydd ORCA
Online Research @ Cardiff 
WelshClear Cookie - decide language by browser settings

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

Dürüst, Yasar, Karakus, Hamza, Kariuki, Benson M. ORCID: 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

[thumbnail of postprint.pdf]
PDF - Accepted Post-Print Version
Download (1MB) | Preview


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 2023 05:42

Citation Data

Cited 2 times in Scopus. View in Scopus. Powered By Scopus® Data

Actions (repository staff only)

Edit Item Edit Item


Downloads per month over past year

View more statistics