Conclusions
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1.
Based on the data of the NMR spectra, primary and secondary 4-amino-3-acetyl-6-methyl-2-pyrones (IV) exist predominantly in tautomeric form (IVA), which contains a stable intramolecular hydrogen bond.
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2.
The chemical shifts of the NH proton in a ring of the chelate type depend importantly on the nature of the substituent attached to the nitrogen atom, and reach their highest value for compounds containing an aromatic substituent.
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3.
In the primaryγ-aminopyrone the chemical shifts of both NH protons differ by ~ 1.6 ppm, while the JN 15,H spin-spin coupling constants differ by 1 Hz.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1114–1118, May, 1972.
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Bogdanov, V.S., Negrebetskii, V.V., Lakhvich, F.A. et al. Study of the structure of 4-amino-3-acetyl-6-methyl-2-pyrones by NMR. Russ Chem Bull 21, 1067–1070 (1972). https://doi.org/10.1007/BF00853770
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DOI: https://doi.org/10.1007/BF00853770