An Improved Synthesis of 1,2,3,4-Tetrahydroisoquinolines via Intramolecular Cyclization of N-Acyl-N-(aryl)methyl-2-(phenylsulfinyl)ethylamine by Pummerer Reaction

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概要

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• 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_2O 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).

• 公益社団法人日本薬学会の論文
• 1997-05-15

著者

• 佐野 武弘

  昭和薬科大学

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• SANO Takehiro

  Showa College of Pharmaceutical Sciences

• TODA Jun

  Showa College of Pharmaceutical Sciences

• Toda J

  Showa Coll. Pharmaceutical Sci. Tokyo Jpn

• SHINOHARA Tatsumi

  Racing Chemistry Laboratories

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