BF3-promoted synthesis of diarylhexahydrobenzo[f]isoquinoline.
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.
Chang
Meng-Yang
MY
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan. mychang@kmu.edu.tw
Lin
Chung-Han
CH
Chen
Yeh-Long
YL
Chang
Ching-Yao
CY
Hsu
Ru-Ting
RT
D001880:Boranes / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D001880:Boranes; D007546:Isoquinolines; C101707:boron trifluoride etherate