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Issue 33, 2017

Base catalysed N-functionalisation of boroxazolidones

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A method for the condensation of boroxazolidones derived from L-valine with aromatic aldehydes, catalysed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene was developed. The preparation and isolation of a series of highly functionalised stable ketimines derived from the reaction of 2,2-diaryl-1,3,2-oxazaborolidin-5-ones with aryl aldehydes is herein described. Several unreported boroxazolidones were prepared by condensation of triethylammonium tetra-arylborates with L-valine in up to 98% yield. The newly synthesised compounds were determined to be moderately cytotoxic against colorectal adenocarcinoma cells, with the best compound in this series having an IC50 of 76 μM. A brief inspection of the effect of the same compound against human brain astrocytoma cells showed an IC50 of 268 μM.

Graphical abstract: Base catalysed N-functionalisation of boroxazolidones

Supplementary files

Article information

20 Mar 2017
02 Apr 2017
First published
10 Apr 2017

This article is Open Access

RSC Adv., 2017,7, 20620-20627
Article type

Base catalysed N-functionalisation of boroxazolidones

J. Raunio, J. Mannoja, T. Nguyen, N. Ahmad, N. M. Kemppainen, R. G. Franzén, M. Kandhavelu and N. R. Candeias, RSC Adv., 2017, 7, 20620 DOI: 10.1039/C7RA03266H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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