Base catalysed -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 2017-04, Vol.7 (33), p.262-2627
Hauptverfasser: Raunio, J, Mannoja, J, Nguyen, T, Ahmad, N, Kemppainen, N. M, Franzén, R. G, Kandhavelu, M, Candeias, N. R
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. 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.
ISSN:2046-2069
DOI:10.1039/c7ra03266h