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
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
复制标题
通过琼斯试剂可调合成3-酰基-2-萘酚和3-取代异香豆素促进2-(4-羟基-丁-1-炔基)苯甲醛的级联反应
DOI：
10.1021/jo401502k
复制
发表时间：
2013-10-18
影响因子：
3.6
通讯作者：
Fan, Xuesen
中科院分区：
文献类型：
--
作者：
He, Yan;Zhang, Xinying;Fan, Xuesen
以2-（4-羟基丁炔基）苯甲醛为原料，通过可调的级联反应合成了3-酰基-2-萘酚和3-取代异香豆素。2-（4-羟基-丁-1-炔基）苯甲醛用0.7当量的Jones试剂在CH 3CN中处理，随后通过用Et 3 N预洗脱的硅胶柱色谱纯化，高效地得到3-酰基-2-萘酚。当相同的底物用3当量的琼斯试剂在丙酮中处理时，另一方面，3-取代异香豆素可以以良好的产率获得。
Novel and efficient synthesis of 3-acyl-2- 1) 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.