Fast and Efficient Green Procedure for the Synthesis of Benzo[5,6]chromene Derivatives and Their Sulfur Analogues in Water by Organocatalyst Potassium Phthalimide-N-oxyl,Synthesis

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Fast and Efficient Green Procedure for the Synthesis of Benzo[5,6]chromene Derivatives and Their Sulfur Analogues in Water by Organocatalyst Potassium Phthalimide-N-oxyl
Synthesis ( IF 2.2 ) Pub Date : 2020-03-02 , DOI: 10.1055/s-0037-1610755
Nasser Etivand ₁ , Jabbar Khalafy ₁ , Mohammad G. Dekamin ₂

Affiliation

A simple, clean, straightforward, and environmentally benign one-pot, three-component reaction of various arylglyoxal monohydrates, β-naphthol, and barbituric acid [pyrimidine-2,4,6(1H,3H,5H)-trione] or thiobarbituric acid in the presence of catalytic amounts potassium phthalimide-N-oxyl (PPINO), as a mild and efficient organocatalyst in aqueous media under reflux conditions is reported. This transformation produced the novel diverse-substituted 12-benzoyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-diones and their sulfur analogues in 82–93% yield via filtration and without utilization of any chromatography. The high yields of products, very simple operation, easy workup, availability of starting materials, green process, and high atom-economy are the main benefits of this synthetic strategy.

中文翻译：

有机催化剂邻苯二甲酰亚胺钾-N-氧基在水中快速合成苯并[5,6]亚甲基苯衍生物及其硫类似物的绿色方法

各种芳基乙二醛一水合物，β-萘酚和巴比妥酸[嘧啶-2,4,6（1 H，3 H，5 H）-三酮]的简单，清洁，直接且对环境有益的一锅三组分反应据报道，在催化量的邻苯二甲酰亚胺-N-氧基钾（PPINO）存在下，在水介质中，在回流条件下，作为一种温和有效的有机催化剂，可以使用硫醇或硫代巴比妥酸。这种转化产生了新颖的，不同取代的12-苯甲酰基-8,12-二氢-9 H-苯并[5,6] chromeno [2,3 - d ]嘧啶-9,11（10 H）-二酮及其硫类似物通过过滤，无需使用任何色谱法，产率为82-93％。这种合成策略的主要优点是产品的高产量，非常简单的操作，容易的后处理，原材料的可获得性，绿色工艺以及高原子经济性。

更新日期：2020-04-21

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