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三氟甲磺酸锌:Friedlander 环合合成功能化喹啉中的高效可重复使用的催化剂。

Zinc triflate: a highly efficient reusable catalyst in the synthesis of functionalized quinolines via Friedlander annulation.

机构信息

Department of Medicinal Chemistry, North East Institute of Science and Technology, Jorhat, Assam, 785 006, India.

出版信息

Mol Divers. 2010 Nov;14(4):841-6. doi: 10.1007/s11030-009-9214-0. Epub 2009 Dec 5.

DOI:10.1007/s11030-009-9214-0
PMID:19960367
Abstract

An environmentally friendly and highly efficient procedure for the preparation of quinolines and fused polycyclic quinolines has been developed by a simple Friedlander annulation reaction of 2-aminoaryl ketone with carbonyl compounds in presence of zinc triflate under microwave irradiation and solvent-free conditions. The reaction also proceeds effectively when In(OTf)(3) was used in lieu of Zn(OTf)(2) as the catalyst. The catalyst can be recovered after the reaction and reused efficiently in subsequent runs.

摘要

一种环境友好且高效的制备喹啉和稠合多环喹啉的方法,是通过 2-芳基氨基酮与羰基化合物在三氟甲磺酸锌存在下,于微波辐射和无溶剂条件下进行简单的 Friedlander 环化反应而开发的。当用三氟化铟(In(OTf)(3))代替 Zn(OTf)(2)作为催化剂时,该反应也能有效地进行。反应后催化剂可以回收,并在后续反应中有效地重复使用。

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本文引用的文献

1
An efficient synthesis of quinolines derivatives promoted by a room temperature ionic liquid at ambient conditions under ultrasound irradiation via the tandem addition/annulation reaction of o-aminoaryl ketones with alpha-methylene ketones.在室温离子液体促进下,于环境条件下通过超声辐射,使邻氨基芳基酮与α-亚甲基酮发生串联加成/环化反应,高效合成喹啉衍生物。
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A highly effective one-pot synthesis of quinolines from o-nitroarylcarbaldehydes.一种由邻硝基芳基甲醛高效一锅法合成喹啉的方法。
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通过使用亚甲蓝(MB)的单电子转移和能量转移途径实现弗里德兰德杂环化反应的发展。
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用于喹啉合成的烷氧基胺热解下的异腈捕获反应。
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Molecular iodine: a highly efficient catalyst in the synthesis of quinolines via Friedländer annulation.分子碘:通过Friedländer环化反应合成喹啉的高效催化剂。
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Quinolines and artemisinin: chemistry, biology and history.喹啉与青蒿素:化学、生物学及历史
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A mild and efficient one-step synthesis of quinolines.一种温和且高效的喹啉一步合成法。
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Highly regioselective Friedländer annulations with unmodified ketones employing novel amine catalysts: syntheses of 2-substituted quinolines, 1,8-naphthyridines, and related heterocycles.使用新型胺催化剂对未修饰的酮进行高度区域选择性的Friedländer环化反应:2-取代喹啉、1,8-萘啶及相关杂环化合物的合成。
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Improved selectivity for the binding of naphthyridine dimer to guanine-guanine mismatch.萘啶二聚体与鸟嘌呤-鸟嘌呤错配结合的选择性提高。
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