Substituent effects in the ring-chain tautomerism of 1,3-diaryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines

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Condensation of Betti base analogue amino naphthols with substituted benzaldehydes led to 1,3-diaryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines (3-9) which proved to be three-component (r1-o-r2) tautomeric mixtures in CDCl3 at 300K. The electronic effects of the 3-aryl groups on the ratios of the ring-chain tautomeric forms at equilibrium could be described by the equation log KX=ρσ++log KX=H. The value of the intercept was found to be strongly influenced by the steric arrangement of the 1,3-diaryl substituents.

Original languageEnglish
Pages (from-to)2877-2884
Number of pages8
Issue number16
Publication statusPublished - ápr. 14 2003


ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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