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 Friedlannder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.
出处
《应用化学》
CAS
CSCD
北大核心
2002年第12期1174-1177,共4页
Chinese Journal of Applied Chemistry
