三组分一锅法无溶剂合成2,4-二芳基取代喹啉衍生物

Solvent-free synthesis of 2,4-diaryl substituted quinoline derivatives via a three-component one-pot procedure

  • 摘要: 报道了一种三组分一锅法无溶剂高效合成2,4-二芳基取代喹啉衍生物的方法. 以易得的芳基胺、芳香醛以及芳基乙烯为反应起始物,芳基胺与芳香醛形成的亚胺中间体在Lewis酸FeCl3催化作用下与芳基乙烯进行4 + 2环加成反应得到2,4-二芳基取代喹啉衍生物. 该反应原子经济性高,是一种简洁有趣的反应模式,以82%~92%产率合成12个2,4-二芳基取代喹啉化合物,为绿色制备喹啉化合物和活性筛选提供基础. 所得产物均经过1H NMR、13C NMR和HRMS的表征确证.

     

    Abstract: In this paper, a solvent-free and efficient method for the synthesis of 2,4-diaryl substituted quinoline derivatives via a three-component one-pot procedure has been reported. Utilizing arylamines, aromatic aldehydes and aryl ethylenes as readily available starting materials, the imine intermediates were generated by arylamines and aromatic aldehydes which then reacted with aryl ethylenes via a 4+2 cycloaddition catalyzed by Lewis acid FeCl3, providing 2,4-diaryl substituted quinoline derivatives. The reaction was a concise and interesting model, possessing high atomic economy, giving twelve 2,4-diaryl substituted quinoline compounds were synthesized at a yield of 82%−92%, which provided the basis for green preparation of quinoline compounds and activity screening. All products were characterized by 1H NMR, 13C NMR and HRMS.

     

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