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Citation: WANG Jin-Jun, WANG Zheng-You, SUN Gong-Quan, ZHAO Yan, JIANG Gui-Ji. Synthesis of 6,7-Methylenedioxy-3-aza(thia)-1(2H,4H) acridone and Its Derivatives[J]. Chinese Journal of Applied Chemistry, ;2002, 19(12): 1174-1177. shu

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

1.
a Department of Applied Chemistry, Yantai University, Yantai 264005;
2.
b Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian;
3.
c Department of Chemistry, Yanbian University, Yanji

Corresponding author: WANG Jin-Jun,
Received Date: 1 April 2002
Available Online: 8 July 2002

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 Friedlännder reaction of 3b with o-amino benzaldehyde derivatives gave quinoline-fusedaza-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.
- azaacridione,
- thiaacridione,
- heterocyclic derivative,
- synthesis
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