Base catalysed N-functionalisation of boroxazolidones
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-oxazaboro...
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Veröffentlicht in: | RSC advances 2017, Vol.7 (33), p.20620-20627 |
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Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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 IC
50
of 76 μM. A brief inspection of the effect of the same compound against human brain astrocytoma cells showed an IC
50
of 268 μM. |
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ISSN: | 2046-2069 2046-2069 |
DOI: | 10.1039/C7RA03266H |