BF3 促进的二芳基六氢苯并[f]异喹啉的合成。

BF3-promoted synthesis of diarylhexahydrobenzo[f]isoquinoline.

机构信息

Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan.

出版信息

Org Lett. 2010 Mar 19;12(6):1176-9. doi: 10.1021/ol100072n.

PMID:20192201

Abstract

An easy and straightforward synthesis of 6,10b-diarylhexahydrobenzo[f]isoquinoline by the repeated treatment of boron trifluoride etherate (BF(3) x OEt(2)) is reported. The overall transformation from 4-arylpiperidin-3-one to benzo[f]isoquinoline proceeds via ring contraction, chain elongation, and intramolecular electrophilic cyclization in moderate yields. It presents a novel rearrangement reaction catalyzed by boron trifluoride etherate and broadens the scope of application.

摘要

本文报道了通过重复使用三氟化硼乙醚（BF(3) x OEt(2)），简便直接地合成 6,10b-二芳基六氢苯并[f]异喹啉的方法。从 4-芳基哌啶-3-酮到苯并[f]异喹啉的整体转化，通过环缩合、链延长和分子内亲电环化，以中等收率进行。该反应呈现出一种由三氟化硼乙醚催化的新型重排反应，拓宽了其应用范围。