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;
Further Information

Publication History

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

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.

    References

  • 1 Dubocovich ML. Rivera-Bermudez MA. Gerdin MJ. Masana MI. Front. Biosci.  2003,  8:  1093 
  • 2a Voronkov AE. Ivanov AA. Baskin II. Palyulin VA. Zefirov NS. Dokl. Biochem. Biophys.  2005,  403:  284 
  • 2b Lira-Rocha A. Espejo-González O. Naranjo-Rodríguez EB. Eur. J. Med. Chem.  2002,  37:  945 
  • 3 Doss SH. Mohareb RM. Elmegeed GA. Luca NA. Pharmazie  2003,  58:  607 
  • 4 Bidylo TI. Yurovskaya MA. Chem. Heterocycl. Compd.  2005,  41:  1339 
  • 5 Pietra S. Farmaco  1958,  13:  75 
  • 6a Pietra S. Farmaco  1957,  12:  946 
  • 6b Daisley RW. Walker J. Eur. J. Med. Chem.  1979,  14:  47 
  • 7 Bachman GB. Picha GM. J. Am. Chem. Soc.  1946,  68:  1599