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

作　　者：王进军[1] 王正有[2] 孙公权[3] 赵岩[1] 姜贵吉[2] 

机构地区：[1]烟台大学应用化学系,烟台264005 [2]延边大学化学系 [3]中国科学院大连化学物理研究所

出　　处：《应用化学》2002年第12期1174-1177,共4页Chinese Journal of Applied Chemistry

摘　　要：通过 1 -氮 (硫 )杂环己二酮与邻氨基椒醛缩合得 6 ,7-二氧亚甲基 -3-氮杂 (硫杂 ) -1 ( 2 H,4 H)吖啶酮3a和 3b;3a与苯肼进行 Fisher环合形成吲哚并硫杂吖啶 7a和 7b,3a与草酸乙酯的 Claisen反应得 β-酮酯 8,进而与噻唑肼缩合生成吡唑并硫杂吖啶 9a和 9b。 3b与邻氨基苯甲醛化合物发生 Friedlannder反应生成喹啉并氮杂吖啶 4 a～ 4 c,与靛红类化合物的 Pfitzing缩合反应得羧基喹啉并氮杂吖啶 5 a～ 5 c;用核磁共振光谱、红外光谱等进行了分子结构表征。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.

关 键 词：6 7-二氧亚甲基-3-氮流(硫杂)-1(2H 4H)吖啶酮 衍生物 氮杂吖啶酮 硫杂吖啶酮 杂环化合物 合成 有机药物 

分 类 号：R914.5[医药卫生—药物化学] O626[医药卫生—药学]