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Facile one-pot synthetic access to libraries of diversely substituted 3-aryl (alkyl)-coumarins using ionic liquid (IL) or conventional base/solvent, and an IL-mediated approach to novel coumarin-bearing diaryl-ethynes
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2020-03-19 , DOI: 10.1016/j.tetlet.2020.151854
Pavankumar Prabhala , Hemantkumar M. Savanur , Suraj M. Sutar , Shruti S. Malunavar , Rajesh G. Kalkhambkar , Kenneth K. Laali

The in-situ formed carbonylimidazole derivatives of Ar(alkyl)-CH2COOH react at r.t. with substituted salicylaldehydes in [BMIM][PF6] or [BMIM][BF4] as solvent, and [PAIM][NTf2] as basic-IL, to produce libraries of 3-aryl(alkyl)coumarins. Whereas these reactions can also be performed with similar efficiency in THF by employing DBU, the IL approach offers easier work-up and recycling of the IL solvent. An IL-mediated approach to the synthesis of novel coumarin-bearing diaryl-ethynes by the Sonogshira reaction is also reported, and the potential for recycling/reuse of the IL solvent is shown.



中文翻译:

使用离子液体(IL)或常规碱/溶剂,以及通过IL介导的新型带有香豆素的二芳基乙炔,可轻松地一锅合成访问不同取代的3-芳基(烷基)-香豆素的文库

原位的Ar形成羰基咪唑衍生物(烷基)-CH 2 COOH在室温反应在[BMIM] [PF取代的水杨醛6 ]或[BMIM] [BF 4 ]作为溶剂,并[派姆] [NTF 2 ]作为碱性-IL,以产生3-芳基(烷基)香豆素的文库。尽管通过使用DBU,这些反应也可以在THF中以相似的效率进行,但IL方法可简化后处理和IL溶剂的回收利用。还报道了通过Sonogshira反应合成新的带有香豆素的二芳基-乙炔的IL介导的方法,并且显示了回收/再利用IL溶剂的潜力。

更新日期:2020-03-19
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