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Synthesis 2004(18): 3043-3046  
DOI: 10.1055/s-2004-834924
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Improved Synthesis of Hydroxyindoles

Lena Lermana, Marta Weinstock-Rosinb, Abraham Nudelman*a
a Chemistry Department, Bar Ilan University, Ramat Gan, 52900, Israel
Fax: +972(3)5351250; e-Mail: nudelman@mail.biu.ac.il;
b Department of Pharmacology, Faculty of Medicine, Hebrew University, Ein Kerem, Jerusalem, 91120, Israel
Further Information

Publication History

Received 2 June 2004
Publication Date:
17 November 2004 (online)

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Abstract

An improved synthetic procedure for the synthesis of 6- and 7-hydroxyindoles is described. In this method, the addition of two chlorine atoms in 1-benzyloxy-4,5-dichloro-2-nitrobenzene (3) and 1-benzyloxy-2,6-dichloro-3-nitrobenzene (9) facilitated the subsequent cyanomethylation step to give substituted cyanomethyl-dichloronitrobenzenes 4 and 10, leading to an overall increase in the yield of the hydroxyindoles 6 and 12.

Key words

indole synthesis - hydroxyindoles - cyanomethylation

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