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.
READ-THROUGH INDUCER AND PHARMACEUTICAL USE THEREOF
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Paragraph 0417-0421, (2020/08/04)
PROBLEM TO BE SOLVED: To provide a novel read-through inducer. SOLUTION: The present invention relates to a compound represented by the general formula (I) [each symbol in the formula is as described in the specification] or a pharmaceutically acceptable
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.
Dehydrogenative Synthesis of Quinolines, 2-Aminoquinolines, and Quinazolines Using Singlet Diradical Ni(II)-Catalysts
Chakraborty, Gargi,Sikari, Rina,Das, Siuli,Mondal, Rakesh,Sinha, Suman,Banerjee, Seemika,Paul, Nanda D.
, p. 2626 - 2641 (2019/02/26)
Simple, straightforward, and atom economic methods for the synthesis of quinolines, 2-aminoquinolines, and quinazolines via biomimetic dehydrogenative condensation/coupling reactions, catalyzed by well-defined inexpensive and easy to prepare singlet diradical Ni(II)-catalysts featuring two antiferromagnetically coupled singlet diradical diamine type ligands are described. Various polysubstituted quinolines, 2-aminoquinolines, and quinazolines were synthesized in moderate to good yields from different low-cost and readily accessible starting materials. Several control experiments were carried out to get insight into the reaction mechanism which shows that the nickel and the coordinated diamine ligands participate in a synergistic way during the dehydrogenation of alcohols.
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.
(DPEPhos)Ni(mesityl)Br: An Air-Stable Pre-Catalyst for Challenging Suzuki-Miyaura Cross-Couplings Leading to Unsymmetrical Biheteroaryls
Sawatzky, Ryan S.,Stradiotto, Mark
, p. 799 - 804 (2018/01/11)
The successful application of (DPEPhos)Ni(mesityl)Br (C1) as a pre-catalyst in the Suzuki-Miyaura cross-coupling of heteroaryl chlorides or bromides and heteroaryl boronic acids is reported. The use of C1 in this context allows for such reactions to be conducted under mild conditions (2 mol% Ni, 25 °C), including cross-couplings leading to unsymmetrical biheteroaryls. Successful transformations of this type involving problematic pyridinyl boronic acid substrates (10 mol% Ni, 60 °C) are also described.
A nickel catalyzed acceptorless dehydrogenative approach to quinolines
Parua, Seuli,Sikari, Rina,Sinha, Suman,Das, Siuli,Chakraborty, Gargi,Paul, Nanda D.
, p. 274 - 284 (2018/01/12)
A general, efficient and environmentally benign, one-step synthesis of substituted quinoline derivatives was achieved by acceptorless dehydrogenative coupling of o-aminobenzylalcohols with ketones and secondary alcohols catalyzed by a cheap, earth abundant and easy to prepare nickel catalyst [Ni(MeTAA)], featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)). A wide variety of substituted quinolines were synthesized in high yields starting from readily available o-aminobenzylalcohols and ketones or secondary alcohols. A few controlled reactions were carried out to establish the acceptorless dehydrogenative nature of the reactions.
Blue-light-promoted carbon-carbon double bond isomerization and its application in the syntheses of quinolines
Chen, Xinzheng,Qiu, Shuxian,Wang, Sasa,Wang, Huifei,Zhai, Hongbin
, p. 6349 - 6352 (2017/08/10)
A blue-light-promoted carbon-carbon double bond isomerization in the absence of any photoredox catalyst is reported. It provides rapid access to a series of quinolines in good to excellent yields under simple aerobic conditions. The protocol is direct, catalyst-free and operationally convenient.
Synthesis of 2-substituted quinazolines by CsOH-mediated direct aerobic oxidative cyclocondensation of 2-aminoarylmethanols with nitriles in air
Yao, Song,Zhou, Kaijing,Wang, Jiabing,Cao, Hongen,Yu, Lei,Wu, Jianzhang,Qiu, Peihong,Xu, Qing
supporting information, p. 2945 - 2951 (2017/07/24)
By using air as the superior oxidant, a highly atom-efficient synthesis of 2-substituted quinazolines is developed by a CsOH-mediated direct aerobic oxidative reaction of the readily available and stable 2-aminoarylmethanols and nitriles. Effectively working as the promoter in the alcohol oxidation, nitrile hydration, and cyclocondensation steps, CsOH is the best base for the reaction. A similar method can also be extended to the synthesis of substituted quinolines starting from methyl ketones instead of nitriles.
Facile synthesis of 2-substituted quinolines and 3-alkynyl-2-aryl-2H-Indazole via SnCl2-mediated reductive cyclization
Sudhapriya, Narayanasamy,Nandakumar, Avanashiappan,Perumal, Paramasivan Thirumalai
, p. 58476 - 58480 (2015/02/19)
A rapid and efficient SnCl2·2H2O mediated synthesis of quinolines and indazoles has been developed using A3-coupling followed by reductive cyclization. The key highlights are the formation of quinoline in a one-pot fashion and indazole through N-N bond formation.
