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Simple manganese carbonyl catalyzed hydrogenation of quinolines and imines

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Chinese Chemical Letters 2020年第7期31卷 1890-1894页

作者： Zelong Wang Lei Chen Guoliang Mao Congyang Wang Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and FunctionCAS Research/Education Center for Excellence in Molecular SciencesInstitute of ChemistryChinese Academy of SciencesBeijing 100190China University of Chinese Academy of Sciences Beijing 100049China Provincial Key Laboratory of Oil&Gas Chemical Technology College of Chemistry and Chemical EngineeringNortheast Petroleum UniversityDaqing 163318China Physical Science Laboratory Huairou National Comprehensive Science CenterBeijing 101400China

Manganese-catalyzed hydrogenation of unsaturated molecules has made tremendous progresses recently benefiting from non-innocent pincer or bidentate ligands for ***,we describe the hydrogenation of quinolines and imines catalyzed by simple manganese carbonyls,Mn2(CO)10 or MnBr(CO)5,thus eliminating the prerequisite pincer-type or bidentate ligands.

关键词： Manganese Hydrogenation quinolines Imines Homogeneous catalysis

Copper-Catalyzed Annulation of Isothiocyanates with Diaryliodonium Salts: Arylation–Cyclization Approach to quinolines

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Copper-Catalyzed Annulation of Isothiocyanates with Diarylio...

中国化学会全国第十二届有机合成化学学术研讨会

作者： Wang,Yuan-Chao Guo,Wei-Si Wen,Li-Rong College of Chemistry and Molecular Engineering Qingdao University of Science and Technology

quinolines are privileged scaffolds in various bioactive natural products and pharmaceuticals.1 Therefore,many methods for the synthesis of quinolines have been developed including Combes quinoline synthesis,Friedlander synthesis,Skraup synthesis and so *** on our previous studies on the diaryliodonium salts,we herein reported a novel copper-catalyze tandem arylation-cyclization process for the preparation of quinolines from readily available isothiocyanates with diaryliodonium salts.

关键词： quinolines isothiocyanate diaryliodonium salts

C-H Functionalization of quinolines via Cu（Ⅱ）-Catalyzed Reaction

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C-H Functionalization of Quinolines via Cu（Ⅱ）-Catalyzed R...

中国化学会第十三届全国有机合成化学学术研讨会

作者： Qiao Li Du Kui Ying Bei-Bei Xu Jun Shen Chao Zhang Peng-Fei College of Material Chemistry and Chemical Engineering Hangzhou Normal University

In recent years,functionalized quinolines are playing a vital role in biological chemistry,pharmaceutical chemistry,and material *** C-H functionalization of quinolines has become a common strategy for these useful ***,we developed a simple and effective synthetic approach for these quinolines derivatives.A series of substituent were introduced onto the 8-aminoquinoline at C-5 position via Cu（Ⅱ）-catalyzed radical *** novel compounds have displayed widely used in many fields.

关键词： quinolines C-H functionalization Cu(Ⅱ)-catalyzed radical cross-coupling

稻壳灰负载FeCl2·2H2O:一个温和高效的多相催化剂用于Friedlnder杂成环反应合成多取代喹啉(英文)

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催化学报 2013年第12期34卷 2200-2208页

作者： Farhad Shirini Somayeh Akbari-Dadamahaleh Ali Mohammad‐Khah Department of Chemistry College of Sciences University of Guilan

Rice husk ash was used as a new, green, and cheap adsorbent for FeCl3. Characterization of the obtained reagent showed that rice husk ash supported FeCl2·2H2O was formed. This reagent is efficient at catalyzing the synthesis of multisubstituted quinolines by the Friedl鋘der heteroannulation of o‐aminoaryl ketones with ketones or β‐diketones under mild reaction conditions. This methodology allows for the synthesis of a broad range of substituted quinolines in high yields and with excellent regioselectivity in the absence of a solvent.

关键词： Rice husk ash Supported FeCl2·2H2O quinolines 2‐Amino benzophenone Solvent‐free Friedlader heteoannulation

Development of efficient solid chiral catalysts with designable linkage for asymmetric transfer hydrogenation of quinoline derivatives

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Chinese Journal of Catalysis 2021年第9期42卷 1576-1585页

作者： Yiqi Ren Lin Tao Chunzhi Li Sanjeevi Jayakumar He Li Qihua Yang State Key Laboratory of Catalysis Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian 116023LiaoningChina University of Chinese Academy of Sciences Beijing 100049China

Developing chiral solid catalysts for asymmetric catalysis is desirable for the elimination of homogeneous catalysis flaws but remains an immense ***,we report the immobilization of TsDPEN on SBA‐15 with an ionic liquid(IL)linkage via the one‐pot reaction of imidazole‐TsDPEN‐N‐Boc with 3‐(trimethoxysilyl)propyl bromide in the SBA‐15 *** coordination to Rh,the chiral solid catalysts could efficiently catalyze quinoline transfer hydrogenation,achieving 97%conversion with 93%ee,which was comparable to their homogeneous *** chiral solid catalyst with the IL linkage afforded much higher turnover frequency than that without the IL linkage(93 h^(–1)vs.33 h^(–1)),attributed to the phase transfer and formate‐enriching ability of the IL ***,the effect of the pH on the reaction rate of the solid catalyst was investigated,preventing reaction rate retardation during the catalytic *** tuning of the linkage group is an efficient approach for catalytic activity improvement of immobilized chiral catalysts.

关键词： Heterogeneous asymmetric catalysis Asymmetric transfer hydrogenation quinolines Imidazolate Ionic liquid N‐(p‐toluenesulfonyl)‐1,2‐diphenylethylenediamine

Exploring binding mode for styrylquinoline HIV-1 integrase inhibitors using comparative molecular field analysis and docking studies

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Acta Pharmacologica Sinica 2004年第7期25卷 104-112页

作者： Xiao-hui MA, Xiao-yi ZHANG, Jian-jun TAN, Wei-zu CHEN, Cun-xin WANG2 College of LifeScience and Bioengineering, Beijing University of Technology, Beijing 100022, China College of Life Science and Bioengineering Beijing University of Technology 北京 100022

AIM: To understand pharmacophore properties of styrylquinoline derivatives and to design inhibitors of HIV-1 integrase. METHODS: Comparative molecular field analysis (CoMFA) was performed to analyze three-dimen- sional quantitative structure-activity relationship (3D-QSAR) of styrylquinoline derivatives. Thirty-eight compounds were randomly divided into a training set of 28 compounds and a test set of 10 compounds. The stability of 3D- QSAR models was proved by the analysis of cross-validated and non-cross-validated methods. Moreover, the binding mode of these compounds and integrase was constructed by AutoDock program. RESULTS: The CoMFA model of the training compounds was reasonably predicted with cross-validated coefficient (q2) and conventional (r2) values (up to 0.696 and 0.754). Then the model was validated by the test set. The resulting CoMFA maps visualized structural requirements for the biological activity of these inhibitors. Docking results showed that a carboxyl group at C-7 and a hydroxyl group at C-8 in the quinoline subunit, bound closely to the divalent metal cofactor (Mg2+) around the integrase catalytic site. Moreover, there is a linear correlation between the binding energy of the inhibitors with integrase and their inhibitory effect. CONCLUSIONS: The present study indicated that the CoMFA model together with docking results could give us helpful hints for drug design as well as interpre- tation of the binding affinity between these inhibitors and integrase.

关键词： HIV integrase inhibitors quinolines comparative molecular field analysis AutoDock

Effects of glucocorticoid and cysteinyl leukotriene 1 receptor antagonist on CD_(34)^+ hematopoietic cells in bone marrow of asthmatic mice

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Chinese Medical Journal 2004年第4期117卷 592-597页

作者：毛辉殷凯生王曾礼李富宇Department of General Surgery West China Hospital 张希龙刘春涛雷松Department of Tumor Biological Therapy West China Hospital Department of Respiratory Medicine Department of Respiratory Medicine West China Hospital

BACKGROUND: Corticosteroids remain the most effective therapy available for asthma. They have widespread effects on asthmatic airway inflammation. However, little is known about the effects of corticosteroids on the production of bone marrow inflammatory cells in asthma. This study observed the effects of glucocorticoid and cysteinyl leukotriene 1 receptor antagonist on CD34+ hematopoietic cells, so as to explore the possible effectiveness of a bone marrow-targeted anti-inflammatory strategy. METHODS: Balb/c mice were sensitized and challenged with ovalbumin (OVA) to establish an asthmatic model. For two consecutive weeks, asthmatic mice were challenged with OVA while being given either prednisone, montelukast, prednisone plus montelukast, or sterile saline solution. The mice were killed 24 hours after the last challenge with OVA, and bronchoalveolar lavage fluid (BALF), peripheral blood, and bone marrow were collected. Eosinophils in peripheral blood and BALF, and nucleated cells in BALF, peripheral blood, and bone marrow were counted. The percentages of CD34+ cells, CD4+ T lymphocytes and CD8+ T lymphocytes among nucleated cells in peripheral blood and bone marrow were counted by flow cytometry. Immunocytochemistry and in situ hybridization were employed to detect expression of CD34 and interleukin (IL)-5Ralpha mRNA (CD34+ IL-5Ralpha mRNA+ cells) among bone marrow hematopoietic cells. RESULTS: Compared with the sterile saline solution group, the number of eosinophils in BALF and peripheral blood, CD34+ cells in peripheral blood and bone marrow, and CD34+ IL-5Ralpha mRNA+ cells in bone marrow of mice from the prednisone and prednisone plus montelukast groups were significantly lower (P

关键词： Acetates Animals Antigens, CD34 Asthma Cell Count Hematopoietic Stem Cells Immunohistochemistry In Situ Hybridization Interleukin-5 Male Mice Mice, Inbred BALB C Prednisone quinolines Research Support, Non-U.S. Gov't

Facile Synthesis of 2-Difluoromethylated Quinoline Derivatives via A One-pot Catalyst-free Process

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Facile Synthesis of 2-Difluoromethylated Quinoline Derivativ...

中国化学会第十四届全国有机合成化学学术研讨会

作者： Zhenhua Fan Jing Han Jie Chen Hui Zhang Weiguo Cao Department of Chemistry Shanghai University Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic Chemistry CAS

quinolines play an important role in organic chemistry, not only as key structural units in many natural products and important pharmaceuticals but also as useful building blocks for various biologically active molecules and functional materials. Nevertheless, to the best of our knowledge, there are no reports regarding the successful synthesis of 2-difluoromethylated quinoline. Herein we report the efficient synthesis of 2-difluoromethylated quinolines via one-pot catalyst-free reaction. We performed the reaction by employing 2-aminobenzonitriles 1 and methyl 4,4-difluorobut-2-ynoate 2 in MeOH. After stirring for 12 h at 60℃, DBU was added, and the mixture was stirred at 60℃ for an additional 1 h. A series of substituted 2-difluoromethylated quinolines 3 were synthesized in moderate yields(Table 1).

关键词： quinolines 4,4-Difluorobut-2-ynoate Difluoromethyl Compounds

A Simple and Efficient Synthesis of 3-Benzoylquinoline-4-carboxylate Derivatives:Reaction of N,N-Dimethyl enaminone and Isatin Catalyzed by TMSCl

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A Simple and Efficient Synthesis of 3-Benzoylquinoline-4-car...

中国化学会第十三届全国有机合成化学学术研讨会

作者： Zhou Pan Xu Hui Lu Ling-Ling Yu Fu-Chao Faculty of Life Science and Technology Kunming University of Science and Technology

quinolines is an important structural unit which exists in natural products and biologically active *** biological activities include antibacterial,antitumor,antileishmanial,antifungal and the treatment of malaria.[1-2] Due to these diverse activities,the synthesis of quinoline derivatives has attracted increasing attention from synthetic and medicinal chemists.[3] Enaminones is versatile substrates in the synthesis of heterocyclic compounds,as they undergo cyclization in various cascade reactions.[4] Interestingly,substituted pyrroloquinolines can be obtained from the reaction of enaminones with isatins,[4 a-g] but less attention has been paid to investigate quinolines reaction of ***,we report a trimethylchlorosilane（TMSCl）-catalyzed cascade cyclization between N,N-dimethyl enaminones and isatins,which proceeded smoothly the synthesis of quinolines in *** this simple procedure,structurally diverse quinoline compounds were rapidly obtained in good to excellent yields.

关键词： quinolines cascade cyclization N,N-dimethyl enaminones