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An anomalous reaction between 2-amino-4-methyloxazole and aldehydes:Aryl and alkyl hydroxymethylation at the 5-position

✍ Scribed by Humaid R. Khan; G. Crank

Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 72 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)95518-7

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✦ Synopsis

2-Amino-4-methyloxazole gives 5-substituted products when treated with aldehydes instead of expected Schiff bases. Reactions of aldehydes and amines, including heterocyclic amines, are generally straight forward and give the expected imines or Schiff bases1'2'3. However, when an equimolar ratio of 2-amino-4-methyloxazole(1) and anisaldehyde was heated in dry toluene, no Schiff base was formed. Instead the sole product of this reaction was colourless crystalline solid (mp 150-151'C) formed in 77% yield. Elemental analysis and mass spectrum (MW234) confirmed that product had a molecular composition C,,H,,N,O, rather than C,, H N 0 (for expected Schiff base). It was 12 2

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