R. Vijn, H. Arts, P. Maas
Feb 1, 1993
Citations
0
Influential Citations
25
Citations
Journal
Journal of Organic Chemistry
Abstract
Oxime derivatives of 5-oxoalkanenitriles (C 6 chain or longer) were cyclized in most cases with a combination of AcCl and Ac 2 O, or Ac 2 O and HCl to 6-substituted 2-(N-acetylamino)pyridines. Alkaline hydrolysis gave the corresponding 2-aminopyridines in overall yields of 40-65%, 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)