氮杂环丙烷与丙二酸二甲酯的串联反应

Tandem reaction of aziridine with dimethyl malonate

环己烷骈联的氮杂环丙烷与丙二酸二甲酯在碱性条件下回流反应,氮杂环丙烷先发生开环反应,生成的中间体在原位发生分子内亲核加成-消除反应,得到关环产物吡咯烷酮衍生物.实验结果表明,在以氢化钠作为碱、1,4-二氧六环作为溶剂回流时,可以得到满意的产率(45%～99%);氮杂环丙烷的氮原子上联有羰基、磺酰基这一类强吸电子基时,对反应有利.

The ring opening reaction of aziridine derived from cyclohexene with dimethyl malonate was occurred in the presence of a base under reflux, followed by the in situ ring closure of the intermediate leading to pyrrolidone derivatives. Experimental results were shown that when Nail were used as a base, and 1,4-dioxane as a solvent under reflux, could get a satisfactory yield（45 ^--99 ~）. With the strong electron-withdrawing atom group like carbonyl group and sulfonyl group, linking to the nitrogen atom of aziridine, the reaction call perform well.