Melatonin Receptor Antagonist Luzindole: A Facile New Synthesis

Authors: Tsotinis, Andrew; Afroudakis, Pandelis A.

Source: Letters in Organic Chemistry, Volume 5, Number 6, September 2008 , pp. 507-509(3)

Publisher: Bentham Science Publishers

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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

Document Type: Research article

Publication date: 2008-09-01

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