Synthesis of 7-[4-Alkoxy-3-methoxy(hydroxy)phenyl]-10,11-dihydro- benzo [c] acridin-8(7H,9H, 12H)-ones and 4-(8-Oxo-7,8,9,10,11,12-hexahydrobenzo[c]acridin-7-yl)- 2-methoxy(ethoxy)phenyl Esters of Carboxylic Acids

摘要

Reactions of azomethines (Schiff bases) prepared from vanillin and vanillal ethers and 1-naphthylamine with cyclohexane-1,3-dione in butanol afforded in 40-64% yields 7-[4-alkoxy-3-methoxy(hydroxy)phenyl]-10,11-dihydrobenzo[c]acridin-8(7H,9H,12H)-ones and 4-(8-oxo-7,8,9,10,1l,12-hexahydrobenzo[C]acridin-7-yl)-2-methoxy(ethoxy)phenyl esters of carboxylic acids. The reaction products presumably formed by the rearrangement of the azomethine adduct with the cyclohexane-1,3-dione proceeding by the type of Hofmann-Martius rearrangement. The structure of compounds synthesized was confirmed by the elemental analysis, UV, IR, and ~1H NMR spectra.