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Synthesis 2011(2): 273-276  
DOI: 10.1055/s-0030-1258361
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Simple Synthesis of Some 2-Substituted Melatonin Derivatives

Natalia A. Lozinskaya*, Sergey E. Sosonyuk, Maria S. Volkova, Michael Yu. Seliverstov, Marina V. Proskurnina, Sergey E. Bachurin, Nikolay S. Zefirov
Chemistry Department, Moscow State University, Leninskie gory, 1, 3, GSP-1, Moscow 119991, Russian Federation
Fax: +7(495)9391620; e-Mail: natalylozinskaya@gmail.com;
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Publication History

Received 17 July 2010
Publication Date:
14 December 2010 (online)

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Abstract

A simple strategy for the synthesis of some 2-substituted melatonin derivatives using p-anisidine as starting material is reported. The key step is a chemoselective reduction of a cyano group in the presence of an appropriate acid anhydride by hydrogenation over Adams’ catalyst or with sodium borohydride in the presence of catalytic amounts of anhydrous nickel(II) chloride. The 2-substituted melatonin derivatives were obtained in six or seven steps from inexpensive p-anisidine in 9-13% overall yield.

Key words

indoles - melatonin derivatives - reductions - medicinal chemistry