通过 Knoevenagel 缩合和还原反应合成 2-芳基-3-磺酰基色满。
Synthesis of 2-Aryl-3-sulfonylchromans via Knoevenagel Condensation and Reduction Protocol.
机构信息
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University Hospital, Kaohsiung Medical University , Kaohsiung 807, Taiwan.
出版信息
J Org Chem. 2017 Dec 1;82(23):12631-12639. doi: 10.1021/acs.joc.7b02392. Epub 2017 Nov 9.
In this article, a concise, easy-operational, and high-yield method for the synthesis of 2-aryl-3-sulfonylchromans is described by two-step routes: (i) NHOAc mediated Knoevenagel condensation of β-ketosulfones and o-hydroxybenzaldehydes in a cosolvent of toluene and THF at reflux for 10 h, and (ii) NaBH promoted regio- and stereocontrolled reduction of the resulting 2-arylchromen-2-ols in a cosolvent of MeOH and THF at rt for 1 h. This protocol provides a highly effective (4+2) annulation via one carbon-oxygen and one carbon-carbon bond formations.
本文描述了一种通过两步法合成 2-芳基-3-磺酰基色满的简洁、易于操作且高产的方法：（i）在甲苯和四氢呋喃的混合溶剂中，用 NHOAc 介导β-酮砜和邻羟基苯甲醛的 Knoevenagel 缩合反应，回流 10 小时；（ii）在甲醇和四氢呋喃的混合溶剂中，用 NaBH 促进所得 2-芳基色满-2-醇的区域和立体选择性还原，室温反应 1 小时。该方案通过一个碳-氧和一个碳-碳键的形成提供了一种高效的（4+2）环加成反应。
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