Health & Environmental Research Online (HERO)


Print Feedback Export to File
7846119 
Journal Article 
BF3-promoted synthesis of diarylhexahydrobenzo[f]isoquinoline 
Chang, MY; Lin, CH; Chen, YL; Chang, CY; Hsu, RT 
2010 
1 
Organic Letters
ISSN: 1523-7060
EISSN: 1523-7052 
12 
6 
1176-1179 
English 
20192201 
WOS:000275379100009 
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.