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• W2106596215 abstract "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)." @default.
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• W2106596215 date "2001-01-01" @default.
• W2106596215 modified "2023-10-18" @default.
• W2106596215 title "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." @default.
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• W2106596215 doi "https://doi.org/10.1248/cpb.49.979" @default.
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