A Practical Regioselective Synthesis of Alkylthio- or Arylthioindoles without the Use of Smelly Compounds Such as Thiols

• Hamashima Toshihiko

  Faculty of Pharmaceutical Sciences, Toho University

• Mori Yoshiaki

  Faculty of Pharmaceutical Sciences, Toho University

• Sawada Kazunori

  Faculty of Pharmaceutical Sciences, Toho University

• Kasahara Yuko

  Faculty of Pharmaceutical Sciences, Toho University

• Murayama Daisuke

  Faculty of Pharmaceutical Sciences, Toho University

• Kamei Yuto

  Coastal Bioenvironment Center, Saga University

• Okuno Hiroaki

  Faculty of Pharmaceutical Sciences, Toho University

• Yokoyama Yuusaku

  Faculty of Pharmaceutical Sciences, Toho University

• Suzuki Hideharu

  Faculty of Pharmaceutical Sciences, Toho University

Abstract

A convenient method for the synthesis of 3-methylthioindoles has been established which does not use smelly compounds such as thiol derivatives. The method, which introduces an alkyl- or arylthio-group into the C³-position of the indole skeleton, was extended to the direct introduction of a methylthio or bromo group at the C²-position using 3-methylthioindoles. No dimerization occurred, and the reaction mechanism was confirmed. The products have the partial structure of potent anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) bromomethylthioindoles (MC 5–8) isolated from marine algae. Furthermore, this reaction could be applied to the synthesis of 3,3-diindolyl thioether which is a core structure of Echinosulfone A.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 61 (3), 292-303, 2013

  The Pharmaceutical Society of Japan

Keywords

• indole
• electrophilic aromatic substitution
• thioether
• sulfoxide
• trifluoroacetic anhydride

Details

• CRID: 1390001204178525952
• NII Article ID: 130002460113
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.c12-00882
• COI: 1:STN:280:DC%2BC3s7pvVSnuw%3D%3D
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 024284048
• PubMed: 23221649
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I024284048
• Web Site: https://www.jstage.jst.go.jp/article/cpb/61/3/61_c12-00882/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed