芳(杂)环并氮杂(氢化)吖啶的合成及其反应机理研究

Synthesis of Aromatic (Heteroaromatic)-Ring-Fused Aza-Acracridines and Study on the Reaction Mechanism

以1 苄基 3,5 哌啶二酮1为起始原料,通过与邻氨基苯甲醛缩合得3 氮杂吖啶酮2,继续与靛红进行Pfitzing反应给出喹啉并氮杂吖啶3;二酮与α 萘胺和对氯苯甲醛的缩合反应,合成了10 氮杂 7 对氯苯基 六氢苯并[C]吖啶酮4,再经脱氢反应生成10 氮杂 7 对氯苯基 四氢苯并[C]吖啶酮5,并讨论了部分化合物形成的反应机理.所合成的新化合物的结构经红外光谱、核磁共振光谱和元素分析予以证实.

3-aza-1(2H, 4H)acridone 2 is synthesized by condensation reaction of 1-aza-3,5- cyclohexadione with o-aminobenzaldehyde. Pfitzing reaction of 2 with isatin forms carboxyl quinoline-fused aza-acridine 3. 10-aza-7-p-chlorobenzyl-hexahydrobenzoacridone 4 is obtained by use of one pot reaction of diketone, naphthylamine and p-chlorobenzaldehyde. The oxidization of 4 with CrO_3 is carried out to give 10-aza-7-p-chlorobenzyl-tetrahydro- benzoacridone 5. The mechanism of the reaction is tentatively discussed and the structures of the compounds are characterized by elemental analysis, IR and ~1 H NMR spectra.