摘要/Abstract
几种氨甲酰基硅烷与四元环氧-3-酮和四元环硫-3-酮在无催化剂甲苯作溶剂的温和条件下，发生亲核加成反应，直接制备了3-羟基-3-杂环丁基酰胺衍生物，收率为56%～85%，为合成含无手性中心的四元杂环药物提供了一种有效途径.通过不同氨甲酰基硅烷的选择，用此方法可合成3-羟基-3-杂环丁基叔酰胺、仲酰胺和伯酰胺衍生物，以及酰氨基带手性中心的3-取代杂环丁基酰胺.通过研究反应的影响因素发现，氨甲酰基硅烷的酰氨基所带基团旳大小是影响反应的重要因素，它既影响反应完成的时间，又影响产物的产率.该反应具有条件温和、副产物少、产物得率高和后处理简单等优点，是有效合成3-羟基-3-杂环丁基甲酰胺的新方法.
关键词: 氨甲酰基硅烷, α-羟基酰胺, 环杂丁基酰胺, 亲核加成, 合成方法
3-Hydroxy-3-heterocyclebutyl amide derivatives were directly synthesized in 56%~85% yields by nucleophilic addition of various carbamoylsilanes to oxetane-3-one or thietane-3-one in toluene under mild and catalyst-free conditions. This method will provide an efficient route for the synthesis of drugs containing four-membered heterocycles which have not additional stereocentres. The procedure can prepare 3-hydroxy-3-heterocyclebutyl tertiary, secondary and primary amides as well as having a stereocentre connecting with nitrogen atom by selecting different carbamoylsilanes. A comparison of the results obtained from reaction of various carbamoylsilanes indicated that the size of group on the amide group was an important factor in the addition reaction, which influenced on both the reaction time and yields. The reaction has the advantages of mild conditions, less by-products, good yield and simple post-treatment, and is a new method for the efficient preparation of 3-hydroxy-3-heterocycle butylamides.
Key words: carbamoylsilane, α-hydroxyamides, heterocyclicbutylamides, nucleophilic addition, synthetic methods
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