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
Letters in Organic Chemistry
Title: Melatonin Receptor Antagonist Luzindole: A Facile New Synthesis
Volume: 5 Issue: 6
Author(s): Andrew Tsotinis and Pandelis A. Afroudakis
Affiliation:
Keywords: Luzindole, melatonin receptor antagonist, ortho-alkynylanilines, nitroolefination, 2-benzyltryptamides
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.
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Cite this article as:
Tsotinis Andrew and Afroudakis A. Pandelis, Melatonin Receptor Antagonist Luzindole: A Facile New Synthesis, Letters in Organic Chemistry 2008; 5 (6) . https://dx.doi.org/10.2174/157017808785740561
DOI https://dx.doi.org/10.2174/157017808785740561 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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