Research On Synthesis Of Acridone Derivatives

In the paper, 5-aryl-1,3-cyclohexanediones were prepared as a building block from aromatic aldehydes, acetone and dimethyl molanate. The 9-amino-1(2H,4H)-acridinol derivatives were synthesized by condensation of 5-aryl-1,3-cyclohexanediones with anthranilonitrile for enamine formations and then were cyclized in refluxing THF in the presence of potassium carbonate and cuprous chloride.In the experiment, there also synthesized 5,13-diamino-6-phenyl-2,3,10,11–tetramethoxyl-6H,7H-quinolino[2,3-a]acridine, when compound 2e's crude product was cyclized in refluxing THF in the presence of potassium carbonate and cuprous chloride without being purified. And it's structure was determined by single-crystal X-ray diffraction study. The crystal is triclinic, space group: P-1, a = 1.06168(15)nm, b = 1.16951(17) nm, c = 1.6020(2) nm,α= 71.380(3)°,β= 77.686(3)°,γ= 66.743(3)°, V = 1.723(4) nm³, Z = 2, Dc = 1.247 g/cm³, F(000) = 692,μ= 0.087 mm^-1, R = 0.0796, wR = 0.1989.In this article, the other synthesis route was used. By condensation of 5-aryl-1,3- cyclohexane-diones with o-aminopiperonal under microwave irradiation, there synthesized 6,7- methylenedioxy-1(2H,4H)-acridinol derivativesAs results, these compounds were successfully substituted on the 3-group by the corresponding heteraromatic rings. And the second experimental results showed that this method provided several advantages such as high yield, short reaction time and simple work-up procedure.The structures of all these new compounds were characterized by elemental analysis, IR and 1H NMR and 13C NMR spectra.