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Novel fused oxobenzopyrano[6,7-d]oxazoles as light-triggered protecting groups for carboxylic acids
Published: 25 October 2010 by MDPI in The 14th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Abstract: In order to evaluate the application of new oxobenzopyrano[6,7-d]oxazoles as photocleavable protecting groups, a series of model alanine and β-alanine ester conjugates were synthesised by reaction with the corresponding halomethylated heterocycles. Photocleavage studies of conjugates in methanol/HEPES buffer (80:20) solution at different wavelengths of irradiation (250, 300 and 350 nm) revealed the quantitative release of the amino acids, the best results being obtained for 8-(chloromethyl)-2-methyl-6-oxo-6H-benzopyrano[6,7-d]oxazole.
Keywords: photocleavable protecting groups,oxobenzopyrano[6,7-d]oxazoles,carboxylic acids