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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Melatonin Receptor Antagonist Luzindole: A Facile New Synthesis

Author(s): Andrew Tsotinis and Pandelis A. Afroudakis

Volume 5, Issue 6, 2008

Page: [507 - 509] Pages: 3

DOI: 10.2174/157017808785740561

Price: $65

Abstract

A new, convenient and high yield route to luzindole, the most commonly used melatonin receptor antagonist, is described. The new method involves the Sonogashira coupling reaction between 2-iodoaniline and 3-phenyl-1-propyne followed by cyclisation of the adduct formed, C-3 indole nitroolefination with 1-(dimethylamino)-2-nitroethylene/TFA, reduction to the respective tryptamine and finally acetylation.

Keywords: Luzindole, melatonin receptor antagonist, ortho-alkynylanilines, nitroolefination, 2-benzyltryptamides

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