A mild high yielding synthesis of oxazole-4-carboxylate derivatives

作者：Ferreira Paula M T^*; Castanheira Elisabete M S; Monteiro Luis S; Pereira Goreti; Vilaca Helena

来源：Tetrahedron, 2010, 66(45): 8672-8680.

DOI：10.1016/j.tet.2010.09.014

• N-Acyl-threonine derivatives
• N-Acyl-beta-halodehydroaminobutyric acids
• Oxazole-4-carboxylates
• Fluorescent probes
• Labelled peptides

Several 2,5-disubstituted oxazole-4-carboxylates were prepared in high yields from the methyl esters of N-acyl-beta-halodehydroaminobutyric acid derivatives by treatment with a 2% solution of DBU in acetonitrile. The scope of this reaction was investigated and it was found that dehydrodipeptides having a beta-bromodehydroaminobutyric acid residue gave the corresponding oxazoles in good yields. The photophysical properties of some of the oxazoles prepared were studied in four solvents of different polarity. All compounds have reasonable high fluorescence quantum yields and a moderate solvent sensitivity, which makes them good candidates to be used as fluorescent probes. One of the fluorescent oxazoles prepared was inserted after cleavage of the methyl ester into two model peptides using a conventional solution phase strategy. The photophysical properties of the labelled peptides were studied in ethanol and water and compared with those of the oxazole. The results obtained showed that the oxazole maintains a good fluorescence level and the same solvent sensitivity when linked to a peptide chain.

• 出版日期2010-11-6