2-[(1H-苯并[d][1,2,3]三氮唑-5-胺基)甲基]-4,6-二氯苯酚的合成

Synthesis of 2-[(1H-benzo[d]triazol-5-ylamino)methyl]-4,6-dichlorophenol

目的:合成神经元型一氧化氮合成酶-谷氨酸能突触后致密度蛋白-95(neuronal nitric oxide synthase with postsynapticdensity protein-95,nNOS-PSD-95)解偶联剂2-[(1H-苯并[d][1,2,3]三氮唑-5-胺基)甲基]-4,6-二氯苯酚。方法:以4-硝基-1,2-苯二胺为原料,经重氮化反应和还原反应后得到5-氨基-1H-苯并[d][1,2,3]三氮唑。5-氨基-1H-苯并[d][1,2,3]三氮唑和3,5-二氯水杨醛缩合形成亚胺,经还原制得目标化合物。结果:目标物结构经核磁共振氢谱(1H-NMR)和核磁共振碳谱(13C-NMR)确证,收率20.3%。结论:该合成方案能简便快速地合成2-[(1H-苯并[d][1,2,3]三氮唑-5-胺基)甲基]-4,6-二氯苯酚。

Objective：To synthesize the uncoupler 2-[（1H-benzo[d]triazol-5-ylamino） methyl]-4,6-dichlorophenol for neuronal nitric oxide synthase（nNOS） with postsynaptic density protein-95（PSD-95）.Methods： 5-amine-1H-benzo[d]triazol was firstly synthesized from 4-nitrobenzene-1,2-diamine by diazotization and reduction.Then the target compound was obtained by reduction after condensation of 5-amine-1H-benzo [d]triazol and 3,5-dichloro-2-hydroxybenzaldehyde.Rusults： The target compound was confirmed by hydrogen nuclear magnetic resonance spectra（1H-NMR） and carbon nuclear magnetic resonance spectra（13C-NMR）,and the overall yield is 20.3%.Conclusion： The program of experiments can be used to synthesize 2-[（1H-benzo[d]triazol-5-ylamino） methyl]-4,6-dichlorophenol quickly and easily.