Events The 14th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 14th International Electronic Conference on Synthetic Organic Chemistry

Published date

25 Oct, 2010

Citation

M. Sameiro T. Gonçalves, Susana P. G. Costa, Ana M. S. Soares, Novel fused oxobenzopyrano[6,7-d]oxazoles as light-triggered protecting groups for carboxylic acids, in Proceedings of The 14th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2010, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-14-00440

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Novel fused oxobenzopyrano[6,7-d]oxazoles as light-triggered protecting groups for carboxylic acids

M. Sameiro T. Gonçalves ¹

Susana P. G. Costa ¹

Ana M. S. Soares ¹

1. Centro de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal

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

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