以邻甲苯胺为起始原料,经3步反应制得4-甲基-2,1,3-苯并噻二唑(1);1经溴代、水解和选择性氧化制得系列4,7-非对称二取代苯并噻二唑砌块;通过砌块4-甲酰基-7-溴-2,1,3-苯并噻二唑与给电子基团的缩合或偶联反应,合成了具有4,7-非对称苯并噻二唑D-π-A型分子结构的新化合物4-甲酰基-7-N,N-二甲氨基-2,1,3-苯并噻二唑和4-甲酰基-7-[4-(N,N-二甲氨基)]苯基-2,1,3-苯并噻二唑,其结构经NMR和HR-MS表征。
Several asymmetrical 4,7-disubstituted-2,1,3-benzothiadiazole blocks were synthesized from 4-methyl-2,1,3-benzothiadiazole(1),which was obtained from o-methylaniline by a 3-step reaction of bromination,hydrolysis and selective oxidation with IBX.New D-π-A type asymmetrical 4,7-disubstituted-2,1,3-benzothiadiazoles,4-formyl-7-(N,N-dimethyl)amino-2,1,3-benzothiadiazole and 4-formyl-7-[4-(N,N-dimethylamino)]phenyl-2,1,3-benzothiazole,were prepared by condensation or coupling reaction of the 4-formyl-7-bormo-2,1,3-benzothiadiazole block with electron-donating groups.The structure were characterized by NMR and HR-MS.