二胺与二酮环聚合反应的不同途径与产物

Different Pathways for the Cyclocondensation Reactions of 1,2-Diamine and 1,2-Diketone

在质子性溶剂中,3,5-二叔丁基-1,2-苯醌分别与双[(三异丙基硅烷基)乙炔基]萘-2,3-二胺和双[(三异丙基硅烷基)乙炔基]蒽-2,3-二胺反应,在不同条件下得到含有吡嗪环的缩合产物1和含有咪唑环的缩合产物2.通过核磁共振波谱、紫外-可见光谱、高分辨质谱及单晶X射线衍射表征确定了产物的结构,并提出了可能的反应机理.

It is generally acknowledged that in protic organic solvents,1,2-diamine reacts with 1,2-diketone to form an aromatic compound containing the pyrazine ring.As expected,the condensation reactions of 1,4-bis-[(triisopropylsilyl)ethynyl]naphthalene-2,3-diamine or 1,4-bis[(triisopropylsilyl)ethynyl]anthracene-2,3-diamine with 3,5-di-tert-butyl-1,2-benzoquinone yielded diazatetracene and diazapentacene derivatives.Meanwhile,naphthoazepin and anthroazepin derivatives which contained the imidazole ring were also obtained.Naphthoazepin and anthroazepin derivatives contained a seven-membered ring.All new compounds were characterized by proton and carbon-13 nuclear magnetic resonance spectroscopy,UV-vis spectrophotometry,high resolution mass spectrometry and single crystal X-ray diffraction.The possible reaction mechanisms were proposed as well.