22191-97-5Relevant articles and documents
Method for synthesizing quinoline derivatives by copper catalysis
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Paragraph 0044-0048, (2021/03/24)
The invention relates to a method for synthesizing quinoline derivatives by copper catalysis. The method comprises the following steps: mixing 2-aminobenzyl alcohol, acetophenone derivatives, an alkaline reagent, a copper catalyst and a nitrogen-containing ligand in an organic solvent, and reacting at room temperature for 6-12h; and after the reaction is finished, sequentially carrying out concentration and column chromatography separation on the obtained reaction solution to obtain the corresponding quinoline derivative. Compared with the prior art, the method has the advantages that 2-aminobenzyl alcohol and acetophenone derivatives which are cheap and easy to obtain are used as raw materials, cuprous iodide CuI or cuprous bromide CuBr with stable properties is used as a catalyst, the quinoline skeleton-containing derivatives are directly constructed, use of toxic reagents is avoided, and the method conforms to the development concept of green chemistry; and the method has the advantages of simple operation, mild reaction conditions, good substrate universality and the like, and has huge application potential in the aspect of drug intermediate synthesis.
Fe2O3@[proline]–CuMgAl–LDH: A magnetic bifunctional copper and organocatalyst system for one-pot synthesis of quinolines and 2H-indazoles in green media
Esfandiary, Naghmeh,Heydari, Akbar
, (2020/05/25)
A novel magnetic core–shell Fe2O3@[proline]–CuMgAl–L(ayered)D(ouble)H(ydroxide) was designed as an efficient bifunctional catalytic system. To this end, Cu (II) was combined with Mg and Al in the LDH structure and l-proline was intercalated between LDH layers in order to perform a straightforward synthesis of quinolines and 2H-indazoles as two important pharmaceutical N-aryl-substituted heterocyclic compounds. In this regard, a facile method was employed through consecutive condensation under a mild conditions in choline azide media, which played the role of a reagent and a solvent to avoid toxic solvents and hazardous azidation reagents. These techniques provided considerable improvement in terms of using green media, reducing starting materials, reaching higher yields and offering a shorter reaction time and lower temperature. In conclusion, it was found that the catalyst could be reused five times with no significant loss of activity.
Metal-Ligand Cooperative Approach to Achieve Dehydrogenative Functionalization of Alcohols to Quinolines and Quinazolin-4(3 H)-ones under Mild Aerobic Conditions
Das, Siuli,Sinha, Suman,Samanta, Deepannita,Mondal, Rakesh,Chakraborty, Gargi,Branda?, Paula,Paul, Nanda D.
, p. 10160 - 10171 (2019/08/20)
A simple metal-ligand cooperative approach for the dehydrogenative functionalization of alcohols to various substituted quinolines and quinazolin-4(3H)-ones under relatively mild reaction conditions (≤90 °C) is reported. Simple and easy-to-prepare air-stable Cu(II) complexes featuring redox-active azo-aromatic scaffolds, 2-arylazo-(1,10-phenanthroline) (L1,2), are used as catalyst. A wide variety of substituted quinolines and quinazolin-4(3H)-ones were synthesized in moderate to good isolated yields via dehydrogenative coupling reactions of various inexpensive and easily available starting materials under aerobic conditions. A few control experiments and deuterium labeling studies were carried out to understand the mechanism of the dehydrogenative coupling reactions, which indicate that both copper and the coordinated azo-aromatic ligand participate in a cooperative manner during the catalytic cycle.
