4-或6-芳基取代的二氢嘧啶-4-酮的合成  

Synthesis of 4-or 6-aryl substituted Dihydropyrimidin-4-ones

作　　者：郭丽婷 李轲 谭重阳 吴滨[1] GUO Liting;LI Ke;TAN Chongyang;WU Bin(School of Pharmaceutical Sciences,South-Central Minzu University,Wuhan 430074,China)

机构地区：[1]中南民族大学药学院,武汉430074

出　　处：《中南民族大学学报（自然科学版）》2022年第2期138-145,共8页Journal of South-Central University for Nationalities：Natural Science Edition

基　　金：国家自然科学基金资助项目(21772236);中央高校基本科研业务费专项资金资助项目(CZT18012);中南民族大学教学改革专题研究项目(JGZX202000)。

摘　　要：报道了一价酮催化N-乙酰基-1-苯基炔丙基胺或N-苯甲酰基-炔丙基胺与对甲基苯磺酰叠氮反应生成4-或6-芳基取代的二氢嘧啶-4-酮的方法.该反应过程首先是发生铜催化的炔与叠氮化物反应生成乙烯亚胺中间体A,紧接着乙烯亚胺中间体A经过分子内环加成得到B,B再经过重排反应生成4-或6-芳基取代的二氢嘧啶-4-酮类化合物.采用该方法合成了21个二氢嘧啶-4-酮类化合物,并且利用X单晶衍射方法确定了产物的结构.二氢嘧啶-4-酮分子骨架存在于多种药物活性分子中,该合成方法为其在药物化学中的应用提供了有力的帮助.A method for the synthesis of 4-or 6-aryl substituted dihydropyrimidin-4-one catalyzed by Cu(I)salt with N-(1-phenylprop-2-yn-1-yl)acetamide or N-benzoyl-2-propynylamine and p-methylbenzenesulfonyl azide is reported.The reaction process is initialed by copper-catalyzed reaction of terminal alkyne with azide to afford intermediate A,which produces intermediate B via intramolecular cycloaddition.B proceeds subsequent rearrangement to afford dihydropyrimidin-4-one.Twenty-one dihydropyrimidin-4-ones were synthesized and the molecular structure was further conformed by an X-ray diffraction.The molecular skeleton of dihydropyrimidinone constructed by this method exists in a variety of drug active molecules,which has important research significance.

关 键 词：环加成反应 乙烯亚胺 重排反应 

分 类 号：O621.3[理学—有机化学]