104151-18-0Relevant academic research and scientific papers
A synthesis of 3-phenyl-1,2,3,4-tetrahydroisoquinoline and 2-phenyl-1,2,4,5-tetrahydro-3H-3-benzazepine via Pummerer-type cyclization: Enhancing effect of boron trifluoride diethyl etherate on the cyclization
Saitoh,Ichikawa,Horiguchi,Toda,Sano
, p. 979 - 984 (2007/10/03)
A synthesis of 6,7-dimethoxy-3-phenyl-1,2,3,4-tetrahydroisoquinoline (14a) and 7,8-dimethoxy-2-phenyl-1,2,4,5-tetrahydro-3H-3-benzazepine (14b) was achieved via the cyclization of N-(3,4-dimethoxyphenyl)methyl-1-phenyl-2-(phenylsulfinyl)ethylformamide (6a) and N-2-(3,4-dimethoxyphenyl)ethyl-1-phenyl-2-(phenylsulfinyl)-ethylformamide (6b) using the Pummerer reaction as a key step, respectively. The Pummerer reaction of 6a,b under usual conditions using trifluoroacetic anhydride yielded the vinyl sulfides (8a, b), non-cyclized products, as a major product. The cyclization proceeded when boron trifluoride diethyl etherate was used as an additive reagent, thus giving rise to the corresponding cyclized products (7a) and (7b) in moderate yields. We propose that the enhancing effect of the Lewis acid on the cyclization may be attributable to the involvement of a dicationic intermediate, sulfonium-carbenium dication (23).
N-acyl-tetrahydroisoquinolines as inhibitors of acyl-coenzyme a:cholesterol acyl transferase
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, (2008/06/13)
N-acyltetrahydroisoquinolines including novel compounds of the formula STR1 wherein R1 is a C10-C25 alkyl chain; a substituted C10-C25 alkyl chain; an interrupted C10-C25 alkyl chain; a substituted interrupted C10-C25 alkyl chain; diphenylamino
