Synthesis and spectral characteristics of 4-(10,10-dimethyl-8-oxo-7,8,9,10,11,12-hexahydrobenzo[c]acridin-7-yl)-2-methoxy(ethoxy)phenyl carboxylates

By reaction of vanillin and ethyl vanillin with 1-naphthylamine in ethanol previously unknown azomethines (Schiff’s bases) were obtained as individual E-isomers which in heterocyclizatoion with dimedone provided in 33–77% yield individual 4-(10,10-dimethyl-8-oxo-7,8,9,10,11,12-hexahydrobenzo[c]acridin-7-yl)-2-methoxy(ethoxy)phenyl carboxylates formed as a result of recombination of the adduct of azomethine and dimedone occurring by the type of Hofmann-Martius rearrangement. The structure of compounds obtained was confirmed by elemental analyses, UV, IR, and 1H NMR spectra.