Synthesis of 5-arylpyrrolo[2,1-a]isoquinolin-3(2H)-ones from N-phenethylsuccinimides and organolithium reagents
作者:M.Isabel Collado、Esther Lete、Nuria Sotomayor、María-Jesús Villa
DOI:10.1016/0040-4020(95)00154-z
日期:1995.4
4-dimethoxyphenyl)ethylsuccinimides 3 with organolithium reagents, the key steps being a carbonphilic addition-cyclization viaN-acyliminium ions and Parham-type cyclization, respectively. In both cases, no competition with the cyclization to the five membered nitrogen ring is observed, which is consistent with the fact that when reacted with organolithium reagents N-benzylsuccinimides 4 did not cyclize
通过N -1的反应,可以有效地制备可以被认为是3-芳基异喹啉衍生物的5-芳基-8,9-二烷氧基吡咯并[2,1-a]异喹啉-3(2H)-ones 1和2。,2-双(3,4-二甲氧基苯基)乙基琥珀酰亚胺3与有机锂试剂的反应,关键步骤分别是通过N-酰亚胺离子进行的亲碳加成环化和Parham型环化。在这两种情况下,均未观察到与五元氮环的环化反应竞争,这与以下事实一致:当与有机锂试剂反应时,N-苄基琥珀酰亚胺4不会环化为相应的吡咯并异吲哚并酮5和6。