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
posted on 2013-10-18, 00:00authored byYan 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.