生物碱季胺盐化合物反应的研究

The Investigation about the Reaction of Naturally Occurring Alkaloid Quaternary Ammonium Salts

目的了解季胺盐与碱作用的化学反应方式。方法阿托品与溴乙腈反应制得季胺盐溴化N-腈甲基阿托品,得到的季胺盐在四氢呋喃中与过量氢化钠反应。为了使反应的研究简化,将阿托品水解为托品醇、再氧化为托品酮,托品酮季胺盐与氢化钠反应。结果溴化N-腈甲基阿托品与过量氢化钠反应得化合物3和化合物4。溴化N-腈甲基托品酮5与氢化钠反应得化合物7。结论阿托品化合物在氢化钠作用下是首先发生Hofm ann消除反应进而环合生成化合物7。

Objective To investigated the reaction situation of quaternary ammonium salts with base. Methods Atropine reacted with bromoacetonitrile to give N-cyanomethyl-atropine bromide which was treated with sodium borohydride. In order to simplify the study, hydrolysis of atropine afforded tropine. Oxidation of tropine with chromic oxide gave tropinone which can be quaternized to 5 in quantitative yield. Quaternary ammonium salts 5 was treated with Nail. Results N-cyanomethyl-atropine bromide was treated with sodium borohydride to give 3 and 4. Reaction of N-cyanomethyl-tropinone bromide with sodium borohydride leads to 7. Conclusion Atropine derivatives react with sodium borohydride to performed Hofmann elimination reaction and cyclize to produce 7.