Hetarenes with a nitrogen bridging atom. 1. Phenacylation of 2-substituted 6-methylpyridines

Abstract

The reaction of 2-X 6-methylpyridines (X = Cl, Br, OMe, OH, ONa) with phenacyl bromides has been studied. It was shown that for X = Cl or Br the reaction products unexpectedly proved to be the previously unknown 5-methyl homologs of oxazolo[3,2-a]pyridinium, the structure of which was confirmed by spectral data and by an alternate synthesis using the acid cyclization of N-phenacyl-6-methylpyrid-2-one. The model compound required for the alternate synthesis was obtained by the phenacylation of 2-methoxy-6-methyl-pyridine, 6-methylpyrid-2-one, and its sodium salt. Competition between N- and O-alkylation was observed in the last two cases. The structures of the N- and O-isomers were assigned on the basis of spectral data and by comparison with the spectra of the lower homologs.

How to Cite
Babaev, E. V.; Efimov, A. V.; Maiboroda, D. A. Chem. Heterocycl. Compd. 1995, 31, 962. [Khim. Geterotsikl. Soedin. 1995, 1104.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01170323