5353-90-2Relevant academic research and scientific papers
Syntheses of 4-indolylquinoline derivatives via reductive cyclization of indolylnitrochalcone derivatives by Fe/HCl
Chen, Wen-Chang,Lin, Chan-Chieh,Kavala, Veerababurao,Kuo, Chun-Wei,Huang, Chia-Yu,Yao, Ching-Fa
, p. 22499 - 22519 (2015)
An easy and efficient procedure for the synthesis of 4-indolylquinoline derivatives is described. This process involves two steps, the first of which is the Michael addition of indole to nitrochalcones promoted by sulfamic acid under solvent free conditions and the second step is a reductive cyclization of the indolylnitrochalcone intermediates to 4-indolylquinoline derivatives by Fe/HCl in ethanol. In both steps, the reactions are clean and the yields of products are high.
Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines
Liu, Yan-Yun,Wei, Yang,Huang, Zhi-Hui,Liu, Yilin
supporting information, p. 659 - 666 (2021/02/06)
A simple and efficient ligand-free Cu-catalyzed protocol for the synthesis of polysubstituted quinolinesviaoxidative cyclization of oxime acetates with 2-aminobenzyl alcohols at room temperature has been developed. The presented approach provides a new synthetic pathway leading to polysubstituted quinolines with good functional group tolerance under mild conditions. Moreover, this transformation can be applied for the preparation of quinolines on a gram scale. Oxime acetates serve as the internal oxidants in the reactions, thus making this method very attractive.
Iron catalyzed metal-ligand cooperative approaches towards sustainable synthesis of quinolines and quinazolin-4(3H)-ones
Mondal, Rakesh,Chakraborty, Gargi,Guin, Amit Kumar,Pal, Subhasree,Paul, Nanda D.
, (2021/10/12)
Herein we report simple, efficient, and economically affordable metal-ligand cooperative strategies for synthesizing quinolines and quinazolin-4(3H)-ones via dehydrogenative functionalization of alcohols. Various polysubstituted quinolines and quinazolin-4(3H)-ones were prepared in good yields via dehydrogenative coupling of readily available alcohols with ketones and 2-aminobenzamides, respectively under air using a well-defined Fe(II)-catalyst, ([FeL1Cl2] (1)) bearing a redox-active azo-aromatic pincer 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline) (L1). Control experiments and mechanistic investigation disclose that the one-electron reduced mono-anionic species [1]? bearing an iron-stabilized azo-anion radical ligand catalyzes these reactions. Both iron and the redox-active arylazo ligand participate synergistically during the different steps of these catalytic reactions.
Ruthenium complex and preparation method thereof and catalytic application
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Paragraph 0104-0106; 0143-0144, (2021/01/24)
The invention discloses a ruthenium complex and a preparation method thereof and catalytic application. The ruthenium complex is reported for the first time. Research finds that the ruthenium complexhas the activity of catalytically synthesizing quinazoline and derivatives thereof or catalytically synthesizing quinoline and derivatives thereof. When the ruthenium complex provided by the inventionis used for catalytic synthesis of quinazoline and derivatives thereof or quinoline and derivatives thereof, the ruthenium complex has the advantages of mild reaction conditions, wide substrate range, high catalytic product yield and good functional group tolerance, and is significantly superior to the prior art.
Efficient access to quinolines and quinazolines by ruthenium complexes catalyzed acceptorless dehydrogenative coupling of 2-aminoarylmethanols with ketones and nitriles
Feng, Qi,Han, Zhangang,Hao, Zhiqiang,Huo, Shuaicong,Kong, Siqi,Lin, Jin,Lu, Guo-Liang,Zeng, Guang
, (2021/09/08)
Treatment of N,N,O-tridentate pyrazolyl-pyridinyl-alcohol ligands, 2-(CR1R2OH)-6-[3,5-(R3)2C3HN2]C5H3N (R1 = R2 = Me, R3 = H (L1H); R1 = Me, R2 = Ph, R3 = H (L2H); R1 = R2 = Ph, R3 = H (L3H); R1 = R2 = R3 = Me (L4H)) with RuCl3?xH2O in refluxing EtOH afforded the corresponding Ru(III) complexes L2RuCl (1a-1d), which were well characterized by IR, HR-MS and X-ray single crystal structural determination. These Ru complexes showed similarly high catalytic performance for both dehydrogenative couplings of 2-aminoarylmethanols with ketones and nitriles, giving the quinolines and quinazolines in good to excellent yields. This protocol provides an atom-economical and sustainable route to access various structurally important quinoline and quinazoline derivatives by using phosphine-free ligand based Ru catalysts.
Superbase-Mediated Indirect Friedl?nder Reaction: A Transition Metal-Free Oxidative Annulation toward Functionalized Quinolines
Rahul,Nitha,Omanakuttan, Vishnu K.,Babu, Sheba Ann,Sasikumar,Praveen, Vakayil K.,Hopf, Henning,John, Jubi
, p. 3081 - 3089 (2020/05/08)
A superbase mediated indirect Friedl?nder reaction towards functionalized quinolines has been realized. The reaction was performed with o-aminobenzyl alcohol and ketones having an active methylene moiety in the presence of KOH and in DMSO. The reaction proceeds predominantly via initial formation of an imine intermediate and subsequent oxidation of the benzyl alcohol functionality and condensation to afford substituted quinolines. We could also demonstrate that a minor fraction of the reaction proceeds via a chalcone intermediate. The transition metal-free oxidative annulation was found to be general affording 2-substituted, 2,3-disubstituted/fused or multi-substituted quinolines. The reaction was extended towards the functionalization of natural products and the applicability of the reaction for gram-scale synthesis of quinolines was also demonstrated.
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-Free Oxidative B?N Coupling of nido-Carborane with N-Heterocycles
Yang, Zhongming,Zhao, Weijia,Liu, Wei,Wei, Xing,Chen, Meng,Zhang, Xiao,Zhang, Xiaolei,Liang, Yong,Lu, Changsheng,Yan, Hong
supporting information, p. 11886 - 11892 (2019/07/18)
A general method for the oxidative substitution of nido-carborane (7,8-C2B9H12?) with N-heterocycles has been developed by using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) as an oxidant. This metal-free B?N coupling strategy, in both inter- and intramolecular fashions, gave rise to a wide array of charge-compensated, boron-substituted nido-carboranes in high yields (up to 97 %) with excellent functional-group tolerance under mild reaction conditions. The reaction mechanism was investigated by density-functional theory (DFT) calculations. A successive single-electron transfer (SET), B?H hydrogen-atom transfer (HAT), and nucleophilic attack pathway is proposed. This method provides a new approach to nitrogen-containing carboranes with potential applications in medicine and materials.
Unsymmetrical triazolyl-naphthyridinyl-pyridine bridged highly active copper complexes supported on reduced graphene oxide and their application in water
Hu, Wenkang,Zhang, Yilin,Zhu, Haiyan,Ye, Dongdong,Wang, Dawei
supporting information, p. 5345 - 5351 (2019/10/11)
A novel unsymmetrical triazolyl-naphthyridinyl-pyridine ligand was designed and synthesized, and employed in the synthesis of a heterogeneous copper complex on reduced graphene oxide. The resulting copper composite was characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and energy dispersive X-ray spectroscopy (EDX). This supported copper catalyst containing unsymmetrical triazolyl-naphthyridinyl-pyridine (only 0.1 mol%) showed excellent catalytic activity in water with good recyclability. Various functionalized quinoline derivatives were successfully synthesized in high yields through the green strategy in water. Other heterocyclic compounds, such as pyridine, 2-(pyridin-2-yl)quinoline, 1,8-naphthyridine, 5,6-dihydronaphtho[1,2-b][1,8]naphthyridine and 2-(pyridin-2-yl)-1,8-naphthyridine derivatives, were achieved in water with more than 80% yields. Mechanism studies revealed that this transformation occurs via dehydrogenation, condensation, and transfer hydrogenation and dehydrogenation processes which was supported by a deuterium labeling experiment.
Synthesis method of polysubstituted quinoline
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Paragraph 0042; 0043; 0044; 0045; 0046; 0075; 0076-0079, (2018/04/02)
The invention discloses a synthesis method of polysubstituted quinolone. The method comprises the step: in an oxygen-containing atmosphere, enabling acetophenone, an aniline compound and dimethyl sulfoxide to react in a pot in the presence of an iron salt and/or ferrous salt catalyst so as to obtain the polysubstituted quinolone. By adopting the method disclosed by the invention, the variety of quinolone derivatives is enriched and more intermediates are provided for medicine synthesis; the synthesis method has the advantages of wide raw material sources, simple steps, moderate reaction conditions and high yield and industrial production is facilitated.
