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以邻氨基二苯甲酮为原料,经两分子环化缩合反应制得6,12-二芳基二苯并[b,f][1,5]二氮杂环辛四烯(2a~2d);2a~2d经Li Al H4还原制得6,12-二芳基-5,6,11,12-四氢二苯并[b,f][1,5]二氮杂环辛(3a~3d);3a~3d与醛(或酮)反应,合成了一系列新型的多取代Trger’s base衍生物(4a~4d和5a~7a),其结构经1H NMR,13C NMR,HR-MS(ESI)和X-射线单晶衍射表征。通过分析架桥前后3a(CCDC:1498564)和6a(CCDC:1498555)的晶体结构,解释了该类化合物1H NMR中NCH质子及桥上取代基质子裂分的原因,并进一步证实了4~7为非C2轴对称结构。
The method of ring-opening condensation of 6,12-diaryldibenzo [b, f] [1,5] diazacyclooctate (2a ~ 2d) with o-aminobenzophenone as starting material ); 2a-2d was reduced with LiAlH4 to give 6,12-diaryl-5,6,11,12-tetrahydrodibenzo [b, f] ~ 3d). A series of novel poly-substituted Trger’s base derivatives (4a ~ 4d and 5a ~ 7a) were synthesized by the reaction of 3a ~ 3d with aldehydes (or ketones). Their structures were confirmed by 1H NMR, 13C NMR, HR- MS (ESI) and X-ray single crystal diffraction. By analyzing the crystal structures of 3a (CCDC: 1498564) and 6a (CCDC: 1498555) before and after bridging, the reasons for the proton splitting between the NCH protons and the bridge substituents in 1H NMR of these compounds were explained and further confirmed that 4 ~ 7 Non-C2 axis symmetrical structure.