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The effect of 6- and 7-substituents on the structure and tautomeric conversions of 3,3-dimethyl-1-(4,4-dimethylcyclohexa-2,6-dion-1-yl)-3,4-dihydroisoquinoline

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Abstract

The crystalline and molecular structure of 3,3-dimethyl-6,7-dimethoxy-1-(4,4-dimethylcyelohexa-2,6-dion-1-yl)-3,4-dihydroisoquinoline (I) have been determined. The effects of 6- and 7- substituents on the structure and tautomeric conversion of 3,3-dimethyl-1-(4,4-dimethylcyclohexa-2, 6-dion-1-yl)-3, 4-dihydroisoquinoline in solution have been studied by IR, electronic, x-ray electronic, and NMR spectroscopy and using quantumchemical calculations in the MNDO/H approximation. It was found that I exists in the enamine-diketone tautomeric form in the crystalline state and in solution. The 6- and 7- substituents cause a change in molecular conformation and a corresponding redistribution of electron density.

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Authors
  1. V. V. Davydov
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  2. V. I. Sokol
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  3. E. V. Balebanova
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  4. Yu. V. Shklyaev
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  5. V. F. Zakharov
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  6. S. L. Kuznetsov
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  7. B. E. Zaitsev
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Additional information

Russian University of National Friendship, Moscow 117198. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow 117000. Institute of Technical Chemistry, Ural Section, Russian Academy of Sciences, Perm' 614600. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 922–933, July, 1995. Original article submitted April 15, 1995.

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Davydov, V.V., Sokol, V.I., Balebanova, E.V. et al. The effect of 6- and 7-substituents on the structure and tautomeric conversions of 3,3-dimethyl-1-(4,4-dimethylcyclohexa-2,6-dion-1-yl)-3,4-dihydroisoquinoline. Chem Heterocycl Compd 31, 803–812 (1995). https://doi.org/10.1007/BF01170740

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