Abstract
On the basis of the application of general valence molecular orbital (VMO) theory it is proposed that nucleophilic substitution of the hydrogen atom in the 5-azacinnoline molecule by indoles should proceed with the participation of the 4-C atom of azacinnoline and the 3-C atom of the indole and that the reaction of the reagents should be intensified in alkaline media in view of an increase in the level of the upper occupied molecular orbital (UOMO) of indole. All of the theoretical assumptions have been confirmed in practice. The corresponding indolylazacinnolines were isolated in the reaction of azacinnoline with indole and 2-methyl- and 1,2-dimethylindoles and were characterized by means of their PMR, UV, and mass spectra. 2,3-Dimethylindole does not undergo reaction.
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