80355-42-6Relevant 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).
Fluoride Ion Promoted Reactions of α-Halo Silanes: Synthesis of Stilbenes, Epoxides, Cyclopropanes, Benzazepines, and Phthalidylisoquinolines
Kessar, Satinder V.,Singh, Paramjit,Kaur, Nachhattar Pal,Chawla, Usha,Shukla, Kalpana,et al.
, p. 3908 - 3912 (2007/10/02)
Reaction of α-halo silanes 1 with CsF in DMF affords stilbenes 5.In the presence of added aldehydes, epoxides 6 are obtained, while with electron-deficient olefins the corresponding cyclopropanes 7 are formed.A similar reaction of 1a with iminium compounds 8 in HMPA leads to 2-phenyl-3-benzazepines 12, whereas 1b or 17 furnishes phthalidylisoquinolines 15.
