BF3-promoted synthesis of diarylhexahydrobenzo[f]isoquinoline

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

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boranes / chemistry*
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Boranes
  • Isoquinolines
  • boron trifluoride etherate