邻羟基芳香N-叔丁基亚磺酰亚胺的微波合成研究

Study on Synthesis of ortho-Hydroxyl Aromatic N-tert-Butylsulfinyl Imines under Microwave Irradiation

手性N-叔丁基亚磺酰亚胺是一类非常重要的有机化学合成中间体.报道以水杨醛类化合物1和N-叔丁基亚磺酰胺(2)为原料,分别以硫酸氢钾、碳酸铯为促进剂在微波辐射条件下反应,合成得到11种未见文献报道的水杨醛类N-叔丁基亚磺酰亚胺(3),产率中等到良好.研究发现:带有强吸电子基的底物在硫酸氢钾的作用下,产率较高;而带有强供电子基化合物、取代基位阻大的化合物在碳酸铯的作用下反应效果较好.所有新化合物均通过红外光谱、核磁共振谱、高分辨质谱对其结构进行了确认.

Chiral N-tert-butanesulfinyl imines have been shown to be important intermediates for asymmetric synthesis in recent years. Eleven new（R,E）-N-（2-hydroxybenzylidene）-tert-butyl-sulfinamides（3） were synthesized from salicylaldehydes 1 and chiral tert-butanesulfinamide 2 under microwave irradiation in moderate to good yields. The reaction could work well in the mixture of KHSO4/PhMe or Cs2CO3/CH2Cl2. And the results show that the KHSO4/PhMe reaction system is helpful for the salicylaldehydes with electron-donating group; however, the Cs2CO3/CH2Cl2 reaction system is applicable to the salicylaldehydes with electron-deficient group and steric hindrance group. The structures of these new compounds were determined by 1H NMR, 13C NMR, IR and HRMS.