877614-70-5Relevant articles and documents
BF3-promoted synthesis of diarylhexahydrobenzo[f]isoquinoline
Chang, Meng-Yang,Lin, Chung-Han,Chen, Yeh-Long,Chang, Ching-Yao,Hsu, Ru-Ting
supporting information; experimental part, p. 1176 - 1179 (2010/05/18)
Chemical Equation Presented An easy and straightforward synthesis of 6,10b-diarylhexahydrobenzo[f]isoquinoline by the repeated treatment of boron trifluoride etherate (BF3·OEt2) is reported. The overall transformation from 4-arylpiperidin-3-one to benzo[f]isoqulnoline 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.
New synthesis of 3-arylpyrrolines
Chang, Meng-Yang,Pai, Chun-Li,Kung, Yung-Hua
, p. 855 - 859 (2007/10/03)
We present an easy and straightforward synthesis of 3-arylpyrrolines 4a-g by repeated treatment of 4-aryl-1,2,5,6-tetrahydropyridines 2a-g with m-chloroperoxybenzoic acid (MCPBA) and boron trifluoride etherate (BF 3-OEt2). The transformation proceeds via epoxidation, ring contraction, Baeyer-Villiger oxidation and elimination reaction and affords 3-arylpyrrolines 4a-g with 61-70% yield. This facile strategy was also used to synthesize racemic baclofen (6).