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

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 methylth...

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Published inChemical and Pharmaceutical Bulletin Vol. 61; no. 3; pp. 292 - 303
Main Authors Toshihiko Hamashima, Yoshiaki Mori, Kazunori Sawada, Yuko Kasahara, Daisuke Murayama, Yuto Kamei, Hiroaki Okuno, Yuusaku Yokoyama, Hideharu Suzuki
Format Journal Article
LanguageJapanese
Published Pharmaceutical Society of Japan 01.03.2013
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Summary: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.
ISSN:0009-2363
1347-5223