Journal of Organic Chemistry p. 887 - 891 (1993)
Update date:2022-07-31
Topics:
Vijn, Robert J.
Arts, Henricus J.
Maas, Peter J.
Castelijns, Anna M.
Oxime derivatives of 5-oxoalkanenitriles (C6 chain or longer) were cyclized in most cases with a combination of AcCl and Ac2O, or Ac2O and HCl to 6-substituted 2-(N-acetylamino)pyridines.Alkaline hydrolysis gave the corresponding 2-aminopyridines in overall yields of 40-65 percent, with the exception of pyridine 3e.Oxime derivatives of 5-oxopentanenitriles did not cyclize but gave glutaronitriles instead.In some experiments with 5-oximinohexanenitrile (1a), 2,4-dimethyl-5-(2-cyanoethyl)oxazole (9) was detected in addition to the main product, 2-(N-acetylamino)-6-methylpyridine (2a).Formation of these compounds can be explained on the basis of a common intermediate 7 formed through rearrangement of the O-acetylated 5-oximinohexanenitrile (4).
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