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Keywords
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1-naphthoates, quinoline, pyranone, cyclohexenone, one-pot, oxidation
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Abstract
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A mild and one-pot synthetic pathway was successfully developed for the synthesis of new naphthoatebased scaffolds containing quinoline, pyranone and cyclohexenone moieties via a multistep reaction
between acenaphthoquinone and various 1,3-diketones in the presence of different primary aliphatic and
benzylic alcohols. This reaction proceeds via a sequential addition/oxidation mechanistic process including a metal-free addition step of acenaphthoquinone and 1,3-diketones followed by the H5IO6-mediated C–C oxidative cleavage of the corresponding vicinal diols at room temperature. The alcohols play a dual role, as the reaction solvent as well as the nucleophile, to conduct the reaction process toward naphthoate formation. All alkyl naphthoate derivatives prepared in this work are new compounds and were definitively characterized using 1 H-NMR, 13C-NMR and HRMS analysis, while X-ray crystallography was carried out for one of the products. The synthesis of a naphthalene-based nucleus attached to heterocyclic moieties is noteworthy to follow in the near future for diverse applications in biology, medicine, metal complex design, and semiconductor and optical materials.
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