6,7-二氧亚甲基-3-氮杂(硫杂)-1(2H,4H)吖啶酮及其衍生物的合成

氮杂吖啶酮;硫杂吖啶酮;杂环化合物;6;7-二氧亚甲基-3-氮杂(硫杂)-1(2H;4H)吖啶酮及其衍生物的合成

Synthesis of 6,7-Methylenedioxy-3-aza(thia)-1(2H,4H) acridone and Its Derivatives

The 6,7-methylenedioxy-3-aza(thia)-1(2H,4H)acridone 3a~3b were synthesized by condensation reaction of 1-aza- or 1-thia-3,5-cyclohexadione with o-aminobenzaldehyde. The Friedlnnder reaction of 3b with o-amino benzaldehyde derivatives gave quinoline-fused aza-acridine 4a~4c. The Pfitzing reaction of 3b with isatin compounds formed carboxyl quinoline-fused aza-acridine 5a~5c. 3a reacted with m-substituted phenylhydrazine to gave indol-fused thia-acridine 7a~7b. From keto-ester 8 prepared by Claisen condensation of 3a with ethyl oxalate two pyroazol-fused thia- acridines 9a~9b were obtained by condensation with thiazolhydrazine. The compositions and structures of all new compounds were characterized by elemental analysis, IR and 1H NMR.