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Tunable Synthesis of 3‑Acyl-2-naphthols and 3‑Substituted Isocoumarins via Jones Reagent Promoted Cascade Reactions of 2‑(4-Hydroxy-but-1-ynyl)benzaldehydes

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posted on 2013-10-18, 00:00 authored by Yan He, Xinying Zhang, Nana Shen, Xuesen Fan
Novel and efficient synthesis of 3-acyl-2-naphthols and 3-substituted isocoumarins via the tunable cascade reactions of 2-(4-hydroxy-but-1-ynyl)­benzaldehydes have been developed. Treatment of 2-(4-hydroxy-but-1-ynyl)­benzaldehydes with 0.7 equiv of Jones reagent in CH3CN and subsequent purification through column chromatography on silica gel pre-eluted with Et3N afforded 3-acyl-2-naphthols with high efficiency. When the same substrates were treated with 3 equiv of Jones reagents in acetone, on the other hand, 3-substituted isocoumarins could be obtained in good yields.

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