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

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.

本研究开发了一种基于2-(4-羟基-1-丁炔基)苯甲醛的可调级联反应，实现了3-酰基-2-萘酚（3-acyl-2-naphthols）与3-取代异色香豆素（3-substituted isocoumarins）的新颖高效合成。将2-(4-羟基-1-丁炔基)苯甲醛与0.7当量的琼斯试剂（Jones reagent）置于乙腈（CH3CN）中反应，随后经以三乙胺（Et3N）预洗脱的硅胶柱色谱进行纯化，即可高效得到3-酰基-2-萘酚。反之，若将相同底物与3当量的琼斯试剂置于丙酮中反应，则可获得良好收率的3-取代异色香豆素。