Intramolecular Capture of Pummerer Reaction Intermediates by an Aromatic Nucleophile : Selective Construction of 1, 4-Benzothiazine and Indole Ring Systems

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概要

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• The simple alkyl sulfoxide 6 carrying two aromatic nucleophiles, when treated with trifluoroacetic anhydride at room temperature (Pummerer reaction conditions), underwent an intramolecular aromatic sulfenylation of the 6-exo-tet process in an exclusive manner to yield two regioisomeric 1, 4-benzothiazine derivatives, 8 and 9. On the other hand, a similar reaction of the α-acyl sulfoxide 7, possessing identical aromatic nucleophiles, caused an intramolecular aromatic alkylation of the 5-exo-trig process to produce the 3-oxo-indole derivative 14 in a quantitative yield. These results demonstrate that the construction of 1, 4-benzothiazine and indole ring systems can be achieved in a selective manner by proper choice of the sulfoxide side chain.

• 公益社団法人日本薬学会の論文
• 2001-09-01

著者

• 佐野 武弘

  昭和薬科大学

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• Toda J

  Showa Coll. Pharmaceutical Sci. Tokyo Jpn

• HORIGUCHI Yoshie

  Shown Pharmaceutical University

• SONOBE Akihiro

  Shown Pharmaceutical University

• SAITOH Toshiaki

  Shown Pharmaceutical University

• TODA JUN

  Shown Pharmaceutical University

• SANO Takehiro

  Shown Pharmaceutical University

• Horiguchi Y

  Showa Pharmaceutical University

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