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1-Butyl-2-methylpipyridinium iodide ([BMPPY]I): novel ionic liquid for the synthesis of 6-hydroxy-6-(1 H -indol-3-yl)indolo[2,1- b ]quinazolin-12(6 H )-ones under green solvent-free conditions
Research on Chemical Intermediates ( IF 2.8 ) Pub Date : 2019-04-17 , DOI: 10.1007/s11164-019-03831-2
Kobra Nikoofar , Seyedeh Shima Peyrovebaghi

Abstract

In this article we reported preparation of 1-butyl-2-methylpipyridinium iodide ([BMPPY]I), as a novel ionic liquid (IL) through simple procedure. This newly prepared IL has been characterized by FT-IR, FESEM, EDX, TGA/DTG, 1H NMR, 13C NMR, and Gc-mass techniques. The FESEM images revealed nano scale for the IL with the average diameter of 150–185 nm. Its efficacy examined for the synthesis of 6-hydroxy-6-(1H-indol-3-yl)indolo[2,1-b]quinazolin-12(6H)-ones via domino three-component reaction of isatin derivatives, isatoic anhydride, and indoles under solvent-free conditions at 100 °C. The results affirmed that ([BMPPY]I) possessed a dual catalytic/solvent role to promote this condensation. Non-flammability, thermal stability, non-toxicity and low cost of the IL that led to obtain pharmaceutically-active heterocycles though easy work-up procedure and short reaction times, are some highlighted features of this green protocol.

Graphical abstract



中文翻译:

1-丁基-2-甲基哌啶碘化物([BMPPY] I):用于合成6-羟基-6-(1 H-吲哚-3-基)吲哚[2,1-b]喹唑啉-12(的新型离子液体) 6 H)-ones在绿色无溶剂条件下

摘要

在本文中,我们通过简单的方法报道了一种新型离子液体(IL)的碘化1-丁基-2-甲基哌啶鎓([BMPPY] I)的制备方法。通过FT-IR,FESEM,EDX,TGA / DTG,1 H NMR,13 C NMR和Gc-mass技术对这种新制备的IL进行了表征。FESEM图像显示IL的纳米级,平均直径为150-185 nm。考察了其合成6-羟基-6-(1 H-吲哚-3-基)吲哚并[2,1 - b ]喹唑啉-12(6 H在100°C下于无溶剂条件下,通过Isatin衍生物,isatoic酸酐和吲哚的多米诺三组分反应进行反应)。结果证实([BMPPY] I)具有双重催化/溶剂作用以促进这种缩合。IL的非易燃性,热稳定性,无毒性和低成本(通过简单的后处理步骤和较短的反应时间)获得了具有药理活性的杂环,是该绿色方案的一些突出特点。

图形概要

更新日期:2019-04-17
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