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- W2034459278 abstract "Pummerer reaction of the sulfoxides 5 of N-acyl-N-(aryl)methyl-2-(phenylthio)ethylamines (4) on treatment with trifluoroacetic anhydride (TFAA) effectively caused intramolecular cyclization under a mild condition to give N-acyl-4-phenylthio-1,2,3,4-tetrahydroisoquinolines (TIQs) (7). The reaction of the N-formyl sulfoxide 5c without a methoxy group in the benzene ring using a formyl group for N-protection is particularly efficient. Treatment of the N-formyl sulfoxide 5f with TFAA did not give any TIQ, but a sequential treatment using TFAA and BF 3 . Et 2 O afforded N-formyl-4-phenylthio-TIQ (7f) in quantitative yield. The efficiency of this method of preparing TIQs was demonstrated in the synthesis of 1,4-dideuterio-TIQ (10D) and its N-methyl derivative (11D)." @default.
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- W2034459278 date "2010-08-03" @default.
- W2034459278 modified "2023-09-26" @default.
- W2034459278 title "ChemInform Abstract: An Improved Synthesis of 1,2,3,4-Tetrahydroisoquinolines via Intramolecular Cyclization of N-Acyl-N-(aryl)methyl-2-(phenylsulfinyl) ethylamine by Pummerer Reaction." @default.
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- W2034459278 doi "https://doi.org/10.1002/chin.199745154" @default.
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