Unexpected reaction of melatonin derivatives with performic acid |
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| Authors: | Zuzanna Molęda Anna Zawadzka Małgorzata Żytek Daria Madej Franciszek Pluciński Jan K Maurin Zbigniew Czarnocki |
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| Institution: | 1. Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warszawa, Poland;2. National Medicines Institute, Che?mska 30/34, 00-725 Warszawa, Poland;3. National Centre for Nuclear Research, So?tana 7, 05-400 Otwock-?wierk, Poland |
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| Abstract: | A series of carbamate melatonin derivatives was treated with performic acid, providing tricyclic products with a 3-hydroxytetrahydropyrrolo2,3-b]indole skeleton. An unusual migration of carbamate groups was observed in some cases, and the reaction appeared to be strongly dependent on the type of substituent in the phenyl ring of the phenylcarbamate group. Theoretical calculations suggest that the reaction is kinetically controlled. |
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| Keywords: | Cyclization Indoles Oxygenations Rearrangement Ring closure |
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