78156-33-9Relevant academic research and scientific papers
STUDIES ON 3,5-DIOXOPIPERIDINES: NOVEL AND FACILE SYNTHETIC ROUTES TO 3-AMINO-5-HYDROXYPYRIDINE DERIVATIVES
Tamura, Yasumitsu,Fujita, Masanobu,Chen, Ling Ching,Kiyokawa, Hiroshi,Ueno, Kyoji,Kita, Yasuyuki
, p. 871 - 874 (2007/10/02)
Three novel synthetic routes to the title compounds were described.Modified Polonovski reaction of 3-acetamido-1-benzyl-5-oxo-3,4-dehydropiperidine (4) or Semmler-Wolff aromatization of 1-benzyl-3-methoxy-5-oxo-3,4-dehydropiperidine oxime (9) followed by reductive debenzylations gave 3-acetamido-5-hydroxypyridine (6) or 3-acetamido-5-methoxypyridine (11), respectively.Nucleophilic replacement of 3,5-dibromopyridine N-oxide (13) with methoxy and amino groups followed by deoxygenation gave 3-amino-5-methoxypyridine (12).
