Studies into the generation and Diels–Alder reactions of 7,8-quinolyne with furan dienes
作者:Gavin E. Collis、Anthony K. Burrell
DOI:10.1016/j.tetlet.2005.03.164
日期:2005.5
organolithium reagents provides the first conclusive route to the intermediate, 7,8-quinolyne. The transient existence of this hetaryne was confirmed by Diels–Alder reactions with furan derivatives that provide endoxide adducts. Chemical induced rearrangement of these adducts allows entry to key compounds of 10-hydroxy[h]benzoquinoline and its 7-substituted derivatives in modest yields.
适当的邻卤代甲苯磺酸盐前体与有机锂试剂的反应提供了通往中间体7,8-喹啉的第一个决定性途径。Diels-Alder与呋喃衍生物的反应证实了这种番石榴碱的瞬时存在,呋喃衍生物提供了内氧化物加合物。这些加合物的化学诱导重排使得能够以适度的收率进入10-羟基[ h ]苯并喹啉及其7-取代衍生物的关键化合物。