- Regioselective synthesis of mixed indole 2,3-bis(sulfides). A study of the mechanism of the second sulfenylation of indole
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Sulfenylation of indole using sulfenyl chlorides leads to the initial formation of a 3-indolyl sulfide, while excess reagent introduces a second sulfide at the 2-position of the ring. The mechanism of this second sulfenylation has not, to date, been rigor
- Hamel, Pierre,Preville, Patrice
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- A practical regioselective synthesis of alkylthio- or arylthioindoles without the use of smelly compounds such as thiols
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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.
- Hamashima, Toshihiko,Mori, Yoshiaki,Sawada, Kazunori,Kasahara, Yuko,Murayama, Daisuke,Kamei, Yuto,Okuno, Hiroaki,Yokoyama, Yuusaku,Suzuki, Hideharu
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p. 292 - 303
(2013/05/08)
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- Acid-catalysed Isomerization of Indol-3-yl Sulphides to Indol-2-yl Sulphides: Unexpected Intermolecular Nature of the Rearrangement
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The rearrangement of indol-3-yl sulphides (1) indol-2-yl sulphides (4), catalysed by proton acids, unexpectedly proceeds by an intermolecular mechanism involving initial disproportionation to an indole-2,3-diyl bis-sulphide (2) and an indole (3), followed by a reaction between (2) and (3) to yield the rearranged product (4).
- Hamel, Pierre,Girard, Yves,Atkinson, Joseph G.
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