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N,N-二磺基哌啶翁双硫酸氢盐([DSPP])[HSO₄]作为高效可回收均相 Brönsted 酸性催化剂,用于涉及 7-烷基或芳基-6H,7H-苯并[f]色烯并[4,3-b]色烯-6-酮的多组分合成研究。

Study of multicomponent synthesis of 7-alkyl or aryl-6H,7H-benzo[f]chromeno[4,3-b] chromen-6-ones involving N,N-disulfopiperidiniumbisulfate [DSPP][HSO] as efficient recyclable homogeneous Brönsted acidic catalyst.

机构信息

Department of Chemical Sciences, Tezpur University, Napaam-784028, Tezpur, Assam, India.

出版信息

Mol Divers. 2024 Feb;28(1):159-169. doi: 10.1007/s11030-023-10642-6. Epub 2023 Apr 13.

Abstract

Herein, a new type of pyranocoumarin derivatives 7-alkyl or aryl-6H,7H-benzo[f]chromeno[4,3-b] chromen-6-ones (2a-h) was developed via three component reaction of 4-hydroxy coumarin, β-naphthol and aliphatic/aryl aldehydes using 25 mol% of N,N-disulfopiperidinium bisulfate [DSPP][HSO] as homogeneous recyclable Brönsted acidic ionic liquid catalyst in EtOAc under reflux to produce excellent yields (89-97%) of the products within 2-4 h reaction. In neat condition, the same reaction required 4.5 h to produce 90% yield of model product (2d) at 100 ℃, which took only 2.5 h to yield 97% of the same product in EtOAc under reflux temperature.

摘要

在此,通过 4-羟基香豆素、β-萘酚和脂肪族/芳族醛的三组分反应,开发了一种新型吡喃香豆素衍生物 7-烷基或芳基-6H,7H-苯并[f]色烯[4,3-b]色烯-6-酮(2a-h),使用 25 mol%的 N,N-二磺基哌啶𬭩双硫酸盐[DSPP][HSO]作为均相可回收 Brönsted 酸性离子液体催化剂,在回流条件下的 EtOAc 中反应,以优异的收率(89-97%)得到产物,反应时间为 2-4 h。在无溶剂条件下,相同的反应需要 4.5 h 才能在 100℃下得到 90%收率的模型产物(2d),而在 EtOAc 回流温度下,仅需 2.5 h 即可得到 97%的相同产物。

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