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

Article abstract of DOI:10.1134/S1070428007100120

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.