I^-/Fe^(3+)体系查尔酮和β-烯胺酮[3+2]反应研究

The [3+2] reaction of chalcone and β-methionone in I^-/Fe^(3+) system

二氢吡咯作为五元含氮杂环的常见的一类简单架构,是一类非常重要的化合物,表现出很高的生物活性.研究了在氯化铁和碘化锌引发条件下,查尔酮和β-烯胺在二氯乙烷作溶剂下发生加成/环合反应,合成了多取代的2,3-二氢吡咯类化合物.此方法采用常见的底物和温和的反应条件,为合成功能化二氢吡咯化合物提供了方便的路径.筛选了该反应的条件为以碳酸钾为碱,在碘化锌和氯化铁存在下,以10%～54%的收率得到2,3-二氢吡咯类化合物衍生物,并通过底物的拓展验证了反应的适用性,共合成了16个化合物.

Dihydropyrrole and its derivatives are a class of important pentatomic heterocyclic compounds.Because of the high biological activities these molecules present and thus have been widely used.A tandem Miachael/cyclization/elimination sequence was studied for the formation of a series of 16 polysubstituted 2,3-dihydropyrroles from chalcones andβ-enamines.The results showed that the optimal parameters were as follows：a mixture of chalcones,1.2 equivalentβ-enamines,1.5 equivalent ZnI2,1.5 equivalent FeCl3 and 1 equivalent K2 CO3 together with 2 mL DCE under 80 ℃ and obtained corresponding products in 10%～54% yields.