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Paper | Regular issue | Vol 24, No. 4, 1986, pp.1019-1024
Published online, 1st January, 1970
DOI: 10.3987/R-1986-04-1019
Synthesis of (5-Hydroxy-2-pyridyl)glycine. Oxazole Formation in the Bucherer-Bergs Reaction. Atudies on Amino Acids VI

Claus Herdeis* and Rolf Gebhard

*Institut für Pharmazie und Lebensmittelchemie, Universität München, Sophienstraße 10, D-80333 München, Germany

Abstract

(5-Hydroxy-2-pyridyl)glycine (1) has been prepared. Bucherer-Bergs reaction of (5-benzyloxy-2-pyridyl)carbaldehyde (6) furnished the oxazole 7b and not the hydantoin 9. Hydrolysis of the oxazole 7b gave the sodium salt of the hydantoic acid 11. After acidic workup the urea derivative 12 was obtained. This demonstrates that the oxazole 7b and not the former postulated isomer 5a is the product of 2-pyridylcarbaldehyde derivatives in the Bucherer-Bergs reaction.