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Syntheses and characterization of new (2S)-2-hydroxy-1,4-oxazin-3-ones derived from β-aminoalcohols

✍ Scribed by Teresa Mancilla; Ma. De Jesus Rosales; Efren V. García-Baez; Lourdes Carrillo

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
338 KB
Volume
6
Category
Article
ISSN
1042-7163

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✦ Synopsis

The reactions of methyl glyoxylate hemiacetal 1 with 2-(methy1amino)ethanol 2, ( I R,2S)-( -)-ephedrine 3 and (IS,2S)-( +) -pseudoephedrine 4 provide the (2s)-2-hydroxy-l,4-oxazin-3-ones 2% 3% 4a i n good yield. They were characterized by 'H, I3C, NMR, and infrared and mass spectroscopy. The structures of 2a and 3a were established by X-ray diffraction. The configuration of C, ( S ) is demonstrated by ' H N M R data and confirmed for compounds 2a and 3a by single-crystal X-ray diffraction studies. 0 I996 John Wiley & Sons, Inc.

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