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SYNTHESIS OF NAPHTHALENIC MELATONIN RECEPTOR LIGANDS

A highly efficient and versatile synthetic approach to the synthesis of naphthalenic analogs of melatonin, compound 7, and its 2-alkyl substituted analog 8 is described. This approach features the novel synthesis of substituted 1-naphthyl acetonitrile 12 and 19 by nucleophilic addition of LiCH2CN to substituted 1-tetralone, followed by aromatization via a 2-step reaction sequence, dehydrogenation with DDQ and TsOH catalyzed dehydration.