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

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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 <i>C</i><sup>3</sup>-position of the indole skeleton, was extended to the direct introduction of a methylthio or bromo group at the <i>C</i><sup>2</sup>-position using 3-methylthioindoles. No dimerization occurred, and the reaction mechanism was confirmed. The products have the partial structure of potent anti-methicillin-resistant <i>Staphylococcus aureus</i> (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

Codes

  • NII Article ID (NAID)
    130002460113
  • NII NACSIS-CAT ID (NCID)
    AA00602100
  • Text Lang
    ENG
  • ISSN
    0009-2363
  • NDL Article ID
    024284048
  • NDL Call No.
    Z53-D167
  • Data Source
    NDL  J-STAGE 
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