Facile synthesis of 2-substituted ethyl 2-(2-amino-5-ethoxycarbonylthiazol-4-yl)ethanoates

摘要

An easy and convenient synthesis of highly functionalized 2-aminothiazole derivatives is described. Ethyl 2-bromo-2-n(2-amino-5-ethoxycarbonylthiazol-4-yl)ethanoate 4 was obtained by reaction of 2,4-dibromo-3-oxoglutarate withnthiourea. It can be transformed to 2-iminoethanoate 10 by nucleophilic displacement of the bromide with an azidenion followed by rearrangement with elimination of the molecule of nitrogen. Hydrolysis of the iminoethanoate 10naffords 2-oxoethanoate 12, while hydrogenation leads to 2-aminoethanoate 14. The crystal structure determination ofn2-iminoethanoate 11 is reported.