一种通过三组分反应合成色烯并[4,3 - b]吡啶的简便方法。
A Convenient Method for the Synthesis of Chromeno[4,3-b]pyridines Via Three-component Reaction.
作者信息
Nikookar Hamideh, Moghimi Setareh, Sayahi Mohammad Hosein, Mahdavi Mohammad, Ranjbar Parviz Rashidi, Firoozpour Loghman, Foroumadi Alireza
机构信息
School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran.
The Institute of Pharmaceutical Sciences (TIPS) and Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.
出版信息
Comb Chem High Throughput Screen. 2018;21(5):344-348. doi: 10.2174/1386207321666180524110635.
AIM AND OBJECTIVE
The importance of Chromeno[4,3-b]pyridines in bioactive compounds, highlighted the ongoing research on developing novel methods for the construction of this heterocyclic scaffold. Regarding the advantageous features of multi-component reactions in organic synthesis, we will try to synthesize pyridocoumarins through this method.
MATERIALS AND METHODS
Chromeno[4,3-b]pyridines were conveniently prepared from a threecomponent condensation reaction between 4-hydroxy coumarin, ammonia and ethyl 2,4-dioxo-4- arylbutanoates in refluxing n-propanol. The synthesized compounds were characterized by NMR, IR and Mass spectroscopy.
RESULTS
The reaction proceeded through an in situ formed 4-amino coumarin, affording eight new target compounds in good yields.
CONCLUSION
This method introduce a novel approach to ethyl 4-aryl-5-oxo-5H-chromeno[4,3- b]pyridine-2-carboxylate derivatives and allow organic chemists to prepare 4-aminocoumarin in reaction medium.
目的与目标
色烯并[4,3 - b]吡啶在生物活性化合物中的重要性，凸显了开发构建这种杂环骨架新方法的持续研究。鉴于多组分反应在有机合成中的优势特性，我们将尝试通过该方法合成吡啶并香豆素。
材料与方法
色烯并[4,3 - b]吡啶可通过4 - 羟基香豆素、氨和2,4 - 二氧代 - 4 - 芳基丁酸乙酯在回流正丙醇中进行的三组分缩合反应方便地制备。合成的化合物通过核磁共振、红外光谱和质谱进行表征。
结果
反应通过原位形成的4 - 氨基香豆素进行，以良好的产率得到了八种新的目标化合物。
结论
该方法为4 - 芳基 - 5 - 氧代 - 5H - 色烯并[4,3 - b]吡啶 - 2 - 羧酸乙酯衍生物引入了一种新方法，并使有机化学家能够在反应介质中制备4 - 氨基香豆素。
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