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