4.4 Article

The first entry to 5,6-dihydroxy-3-mercaptoindole, 5-hydroxy-3-mercaptoindole and their 2-carbomethoxy derivatives by a mild thiocyanation/reduction methodology

Journal

TETRAHEDRON LETTERS
Volume 48, Issue 22, Pages 3883-3886

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.03.141

Keywords

5,6-dihydroxy-3-thioindoles; 5-hydroxy-3-thioindoles; thiocyanation; samarium iodide reduction

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The hitherto unknown 5,6-dihydroxy-3-mercaptoindole (4a) and its 2-carbomethoxy derivative (4b), as well as the analogous 5-hydroxy 3-mercaptoindoles, have been conveniently obtained as O,S-acetyl derivatives 3a-d by thiocyanation of the corresponding acetoxyindoles 1a-d with the NH4SCN/oxone system followed by SMI2 reduction and acetylation. (C) 2007 Elsevier Ltd. All rights reserved.

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