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

Abstract

The crystalline and molecular structure of 3,3-dimethyl-6,7-dimethoxy-1-(4,4-dimethylcyclohexa-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 quantum-chemical 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.

How to Cite
Davydov, V. V.; Sokol, V. I.; Balebanova, E. V.; Shklyaev, Yu. V.; Zakharov, V. F.; Kuznetsov, S. L.; Zaitsev, B. E. Chem. Heterocycl. Compd. 1995, 31, 803. [Khim. Geterotsikl. Soedin. 1995, 922.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01170740