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 C 3 -position of the indole skeleton, was extended to the direct introduction of a methylthio or bromo group at the C 2 -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.
A Practical Regioselective Synthesis of Alkylthio-or Arylthioindoles Without the Use of Smelly Compounds such as Thiols. -A series of 3-alkylthio-and 3-arylthioindoles is prepared by treatment of indoles with sulfoxides and TFAA followed by dealkylation of resulting sulfonium perchlorates in refluxing dipropylamine. -(HAMASHIMA, T.; MORI, Y.; SAWADA, K.; KASAHARA, Y.; MURAYAMA, D.; KAMEI, Y.; OKUNO, H.; YOKOYAMA, Y.; SUZUKI*, H.; Chem. Pharm. Bull. 61 (2013) 3, 292-303, http://dx.doi.org/10.1248/cpb.c12-00882 ; Fac. Pharm. Sci., Toho Univ., Funabashi, Chiba 274, Japan; Eng.) -R. Staver 33-129
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