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-alpyridinium, 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.
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M. V. Lomonosov Moscow State University, Moscow 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1104–1111, August, 1995. Original article submitted July 9, 1995.
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Babaev, E.V., Efimov, A.V. & Maiboroda, D.A. Hetarenes with a nitrogen bridging atom 1. Phenacylation of 2-substituted 6-methylpyridines. Chem Heterocycl Compd 31, 962–968 (1995). https://doi.org/10.1007/BF01170323
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DOI: https://doi.org/10.1007/BF01170323