- Aza-boron-diquinomethene complexes bearing N-aryl chromophores: Synthesis, crystal structures, tunable photophysics, the protonation effect and their application as pH sensors
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A series of aza-boron-diquinomethene complexes (1a-1e) bearing different N-aryl chromophores were synthesized and characterized by multinuclear NMR spectroscopy, X-ray crystallography, optical absorption and emission spectroscopy, and elemental analysis. These robust thermal complexes possess tunable intense luminescence from blue to red with relatively high emission quantum yields. The introduction of different N-aryl chromophores into the aza-BODIQU core significantly tuned the emission colors. The relationship between their structures and properties was investigated systematically via spectroscopic methods and simulated by density functional theory (DFT) calculations. Additionally, the application of 1c as a pH sensor with a remarkable colour-changing property has been investigated. All these results indicate that these complexes exhibit robust thermal stability, tunable photophysical properties, relatively high photoluminescence quantum yields and protonation effect, making these complexes potential candidates for pH sensors, bioimaging probes and organic light-emitting materials.
- Zhu, Xiaolin,Huang, Hai,Liu, Rui,Jin, Xiaodong,Li, Yuhao,Wang, Danfeng,Wang, Qiang,Zhu, Hongjun
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Read Online
- 2-Position-selective C[sbnd]H fluoromethylation of six-membered heteroaryl N-oxides with (fluoromethyl)triphenylphosphonium iodide
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A mild and efficient method for the regioselective C[sbnd]H fluoromethylation of heteroaryl N-oxides with (fluoromethyl)triphenylphosphonium iodide is presented. With LiOt-Bu as the base and DMSO as the solvent, this reaction delivers a series of C2-fluor
- Hu, Chen-Chen,Hu, Wei-Qiang,Qing, Feng-Ling,Xu, Xiu-Hua
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- From Pyridine- N-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy
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The reactions of pyridine-N-oxides with Ph3P under the developed conditions provide an unprecedented route to (pyridine-2-yl)phosphonium salts. Upon activation with DABCO, these salts readily serve as functionalized 2-pyridyl nucleophile equivalents. This umpolung strategy allows for the selective C2 functionalization of the pyridine ring with electrophiles, avoiding the generation and use of unstable organometallic reagents. The protocol operates at ambient temperature and tolerates sensitive functional groups, enabling the synthesis of otherwise challenging compounds.
- Bugaenko, Dmitry I.,Yurovskaya, Marina A.,Karchava, Alexander V.
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supporting information
p. 6099 - 6104
(2021/08/03)
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- Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides
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Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.
- Bhuyan, Samuzal,Chhetri, Karan,Hossain, Jagir,Jana, Saibal,Mandal, Susanta,Roy, Biswajit Gopal
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supporting information
p. 5049 - 5055
(2021/07/29)
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- Reaction of Pyridine-N-Oxides with Tertiary sp2-N-Nucleophiles: An Efficient Synthesis of Precursors for N-(Pyrid-2-yl)-Substituted N-Heterocyclic Carbenes
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N-(Pyrid-2-yl)-substituted azolium and pyridinium salts, precursors for hybrid NHC-containing ligands, were obtained with excellent regioselectivity, employing a deoxygenative CH-functionalization of pyridine-N-oxides with substituted imidazoles, thiazoles, and pyridine. Unlike the traditional SNAr-based methods, this approach provides high yields for substrates bearing substituents of different electronic nature. The utility of azolium and pyridinium salts thus prepared was also highlighted by the synthesis of pyridyl-substituted imidazolyl-2-thione, benzodiazepine as well as 2-aminopyridines.
- Bugaenko, Dmitry I.,Karchava, Alexander V.,Yurovskaya, Marina A.
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supporting information
p. 5777 - 5782
(2020/12/01)
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- COMPOSITIONS FOR THE TREATMENT OF BRAIN TUMORS
-
The instant invention describes pharmaceutical compositions and dosing regimens comprising radiation therapy and seviteronel with or without dexamethasone, and methods of treating diseases, disorders or symptoms thereof.
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Page/Page column 55
(2020/05/19)
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- Hypervalent Iodine(III)-Mediated Regioselective Cyanation of Quinoline N-Oxides with Trimethylsilyl Cyanide
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A regioselective cyanation of quinoline N-oxides with trimethylsilyl cyanide was developed by using (Diacetoxyiodo) benzene (PIDA) as mediated hypervalent iodine(III) reagent under metal-free and base-free reaction conditions to obtain 2-cyanoquinolines. The efficient PIDA reagent could play the role of an activator of the substrates and an accelerator of N?O bond cleavage. The reaction system featured a wide range of substrate suitability and high yields. The procedure was enlarged gram-scale to synthesize the tuberculosis (TB) inhibitor. Finally, according to some experimental results, a plausible mechanism for the cyanation reaction is proposed. (Figure presented.).
- Xu, Feng,Li, Yuqin,Huang, Xin,Fang, Xinjie,Li, Zhuofei,Jiang, Hongshuo,Qiao, Jingyi,Chu, Wenyi,Sun, Zhizhong
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supporting information
p. 520 - 525
(2018/12/13)
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- Rh/O2-Catalyzed C8 Olefination of Quinoline N-Oxides with Activated and Unactivated Olefins
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The rhodium/O2 system-catalyzed distal C(sp2)-H olefination of quinoline N-oxides is developed. Molecular oxygen has been explored as an economic and clean oxidant, an alternative to inorganic oxidants. A wide substrate scope with respect to quinoline N-oxides and olefins (activated acrylates and styrenes; unactivated aliphatic olefins) demonstrates the robustness of the developed catalytic method. Interestingly, 2-substituted quinoline N-oxides also afforded good yields of the corresponding C8-olefinated products. Kinetic isotope studies and deuterium-labeling experiments have been performed to understand the preliminary mechanistic pathway. The applicability of the developed method is demonstrated by utilizing natural product-derived substrates and by converting the C8-olefinated quinoline N-oxides into various other useful molecules.
- Sharma, Ritika,Kumar, Rakesh,Sharma, Upendra
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p. 2786 - 2797
(2019/02/26)
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- Catalyst-Free Synthesis of 2-Anilinoquinolines and 3-Hydroxyquinolines via Three-Component Reaction of Quinoline N-Oxides, Aryldiazonium Salts, and Acetonitrile
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A rapid microwave-assisted, catalyst-free, three-component synthesis of various 2-anilinoquinolines from quinoline N-oxides and aryldiazonium salts in acetonitrile under microwave irradiation is reported. This reaction utilizes acetonitrile as a single nitrogen source and involves the formation of two new C-N bonds via the formal [3 + 2] cycloaddition reaction. In the case of 2-substituted quinolines, 3-hydroxyquinoline was observed as the main product via a 1,3 shift of the oxygen atom from N-oxide to the C3 position of quinolines.
- Dhiman, Ankit Kumar,Chandra, Devesh,Kumar, Rakesh,Sharma, Upendra
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p. 6962 - 6969
(2019/06/14)
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- 2-Position-Selective Trifluoromethylthiolation of Six-Membered Heteroaromatic Compounds
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The regioselective C-H trifluoromethylthiolation of six-membered heteroaromatic compounds via nucleophilic attack of a CF3S source on the electrophilically activated six-membered heteroaromatic ring was developed. The reaction proceeds in good yield with good functional group tolerance, even on a gram-scale. The key to the successful regioselective transformation is the presence of an additive (2,4-dinitrobenzenesulfonyl chloride). The regioselective trifluoromethylthiolation of quinidine derivative is also demonstrated. Trifluoromethylthiolation, followed by S-oxidation, affords the corresponding sulfones.
- Muta, Ryuhei,Torigoe, Takeru,Kuninobu, Yoichiro
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supporting information
(2019/06/13)
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- Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors
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General methods to prepare chiral N-heterocyclic molecular scaffolds are greatly sought after because of their significance in medicinal chemistry. Described here is the first general catalytic methodology to access a wide variety of chiral 2- and 4-substituted tetrahydro-quinolones, dihydro-4-pyridones, and piperidones with excellent yields and enantioselectivities, utilizing a single catalyst system.
- Guo, Yafei,Harutyunyan, Syuzanna R.
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supporting information
p. 12950 - 12954
(2019/08/07)
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- Synergy of anodic oxidation and cathodic reduction leads to electrochemical deoxygenative C2 arylation of quinoline: N-oxides
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The first example of electrochemical deoxygenative C2 arylation of quinoline N-oxides using sulfonyl hydrazines was demonstrated in this work. By employing both anodic oxidation and cathodic reduction, a variety of 2-arylquinolines were synthesized under metal catalyst-, exogenous-oxidant-, and exogenous-reductant-free conditions.
- Yuan, Yong,Jiang, Minbao,Wang, Tao,Xiong, Yunkui,Li, Jun,Guo, Huijiao,Lei, Aiwen
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supporting information
p. 11091 - 11094
(2019/09/20)
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- COMPOSITIONS FOR THE TREATMENT OF BRAIN TUMORS
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The instant invention describes pharmaceutical compositions and dosing regimens comprising seviteronel and/or dexamethasone, and methods of treating diseases, disorders symptoms thereof.
- -
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Page/Page column 51-52
(2019/10/15)
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- Exogenous-oxidant-and catalyst-free electrochemical deoxygenative C2 sulfonylation of quinoline: N-oxides
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An exogenous-oxidant-and catalyst-free electrochemical deoxygenative C2 sulfonylation reaction has been achieved. By employing quinoline N-oxides as the starting materials, the electrochemical C-H sulfonylation of electron-deficient quinolines was indirectly achieved at room temperature and a variety of sulfonylated quinoline derivatives were synthesized in modest to high yield with excellent regioselectivity. Notably, this protocol is the first example for synthesizing sulfonylated electron-deficient heteroarenes/arenes through electrochemistry.
- Jiang, Minbao,Yuan, Yong,Wang, Tao,Xiong, Yunkui,Li, Jun,Guo, Huijiao,Lei, Aiwen
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supporting information
p. 13852 - 13855
(2019/11/21)
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- Simple and scalable electrochemical synthesis of 2,1-benzisoxazoles and quinoline: N -oxides
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Cathodic reduction of the nitro moiety and subsequent intramolecular cyclization affords different substituted 2,1-benzisoxazoles and quinoline N-oxides. This methodology allows the synthesis of two different types of heterocycles from common simple starting materials, using electrons as a sole reagent for this transformation. The electrolysis can be conducted in a very simple undivided electrolysis cell under constant current conditions. This permits working on a larger scale compared to other electrochemical methodologies and represents a significant advantage.
- Rodrigo, Eduardo,Baunis, Haralds,Suna, Edgars,Waldvogel, Siegfried R.
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p. 12255 - 12258
(2019/10/22)
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- Method for synthesizing quinoline oxynitride from quinoline compound by ultrasonic-assisted oxidation
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The invention discloses a method for synthesizing quinoline oxynitride from a quinoline compound by ultrasonic-assisted oxidation. The quinoline compound and hydrogen peroxide are subjected to nitrogen oxidation reaction under the ultrasonic-assisted condition and perfluorosulfonic acid resin (Nafion-H) catalytic action to obtain quinoline oxynitride. The method has the advantages that the raw materials are easy to obtain, reaction conditions are simple and mild, greenness and energy conservation are achieved, and reaction selectivity and yield are high; energy is saved and the compatibility of substrate functional groups is excellent; in particular, the perfluorosulfonic acid resin can be recycled as an acid catalyst, so that not only is the reaction cost reduce, but also the reaction yield is increased, also the pollution problem in traditional oxidation reaction is avoided and a relatively high application value is achieved.
- -
-
Paragraph 0076; 0077; 0078
(2018/06/21)
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- Activation of 6-bromoquinoline by nitration: Synthesis of morpholinyl and piperazinyl quinolones
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Quinoline forms the key skeletal component of a number of important natural products and pharmacologically-Active compounds. Despite a tremendous amount of research pertaining to the derivatization of quinoline, very few general synthetic routes are described in the literature starting from quinoline or tetrahydroquinoline. A simple and convenient method for the polyfunctionalization of quinolines via nitration of bromoquinolines has been developed. This method represents a new synthetic approach to convert brominated nitroquinoline derivatives into useful cyclic amines via nucleophilic-substitution (SNAr) reaction. Formula parented.
- ?akmak, Osman,?kten, Salih,Alimli, Dilek,Saddiqa, Aisha,Ersanli, Cem C?neyt
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p. 362 - 374
(2018/07/05)
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- Quinoline-Flanked Diketopyrrolopyrrole Copolymers Breaking through Electron Mobility over 6 cm2 V?1 s?1 in Flexible Thin Film Devices
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Herein, the design and synthesis of novel π-extended quinoline-flanked diketopyrrolopyrrole (DPP) [abbreviated as QDPP] motifs and corresponding copolymers named PQDPP-T and PQDPP-2FT for high performing n-type organic field-effect transistors (OFETs) in flexible organic thin film devices are reported. Serving as DPP-flankers in backbones, quinoline is found to effectively tune copolymer optoelectric properties. Compared with TDPP and pyridine-flanked DPP (PyDPP) analogs, widened bandgaps and strengthened electron deficiency are achieved. Moreover, both hole and electron mobility are improved two orders of magnitude compared to those of PyDPP analogs (PPyDPP-T and PPyDPP-2FT). Notably, featuring an all-acceptor-incorporated backbone, PQDPP-2FT exhibits electron mobility of 6.04 cm2 V?1 s?1, among the highest value in OFETs fabricated on flexible substrates to date. Moreover, due to the widened bandgap and strengthened electron deficiency of PQDPP, n-channel on/off ratio over 105 with suppressed hole transport is first realized in the ambipolar DPP-based copolymers.
- Ni, Zhenjie,Dong, Huanli,Wang, Hanlin,Ding, Shang,Zou, Ye,Zhao, Qiang,Zhen, Yonggang,Liu, Feng,Jiang, Lang,Hu, Wenping
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- Visible Light-Mediated Decarboxylative Alkylation of Pharmaceutically Relevant Heterocycles
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A net redox-neutral method for the decarboxylative alkylation of heteroarenes using photoredox catalysis is reported. Additionally, this method features the use of simple, commercially available carboxylic acid derivatives as alkylating agents, enabling the facile alkylation of a variety of biologically relevant heterocyclic scaffolds under mild conditions.
- Sun, Alexandra C.,McClain, Edward J.,Beatty, Joel W.,Stephenson, Corey R. J.
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supporting information
p. 3487 - 3490
(2018/06/26)
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- RhIII-Catalyzed Direct C8-Arylation of Quinoline N-Oxides using Diazonaphthalen-2(1H)-ones: A Practical Approach towards 8-aza BINOL
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An efficient RhIII-catalyzed redox-neutral method for the direct C8-arylation of quinoline N-oxides using diazonaphthalen-2(1H)-one as coupling partner has been demonstrated. The developed method is simple, scalable and straightforward with a w
- Ghosh, Bidhan,Biswas, Aniruddha,Chakraborty, Soumen,Samanta, Rajarshi
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supporting information
p. 2388 - 2392
(2018/05/30)
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- Intermolecular Amidation of Quinoline N-Oxides with Arylsulfonamides under Metal-Free Conditions
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An efficient method for the synthesis of N-(quinolin-2-yl)sulfonamides is described. The intermolecular amidation of quinoline N-oxides with sulfonamides proceeded smoothly in the presence of PhI(OAc)2 and PPh3 to afford N-(quinolin-
- Yu, Xiaoqiang,Yang, Sana,Zhang, Yue,Guo, Mingju,Yamamoto, Yoshinori,Bao, Ming
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supporting information
p. 6088 - 6091
(2017/11/27)
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- Metal-free phosphonation of heteroarene N-oxides with trialkyl phosphite at room temperature
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A new protocol is described for the conversion of heteroarene N-oxides to heteroarylphosphonates through in situ activation with bromotrichloromethane. The N-oxides of isoquinoline, quinoline, quinoxaline and 1,10-phenanthroline were fast transformed into the corresponding heteroarylphosphonates in up to 92% yield under mild conditions in the absence of solvent and metal catalysts. The good functional group tolerance, low cost, feasibility of scale up, and wide availability of reagents make this method a prominent complement to the Hirao coupling.
- Chen, Ming-Tao,You, Xia,Bai, Li-Gang,Luo, Qun-Li
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supporting information
p. 3165 - 3169
(2017/04/21)
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- Copper-Catalyzed Direct, Regioselective Arylamination of N-Oxides: Studies to Access Conjugated π-Systems
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An efficient copper(I)-catalyzed direct regioselective arylamination of various heterocyclic N-oxides was achieved successfully under redox-neutral conditions using anthranils as arylaminating reagents. The developed protocol is simple, straightforward, and economic with a broad range substrate scope. The dual functional groups in the final molecules were utilized to construct structurally and functionally diverse nitrogen-containing organic π-conjugated systems.
- Biswas, Aniruddha,Karmakar, Ujjwal,Nandi, Shiny,Samanta, Rajarshi
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p. 8933 - 8942
(2017/09/11)
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- Catalyst and solvent-free alkylation of quinoline N-oxides with olefins: A direct access to quinoline-substituted α-hydroxy carboxylic derivatives
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A catalyst/solvent-free, one-pot and operationally simple method for the synthesis of quinoline-substituted α-hydroxy carboxylic derivatives by the hydroxyheteroarylation of olefins with quinoline N-oxides is reported. The reaction features a high atom-economy, mild and reagent/solvent-free conditions, broad substrate scope and good selectivity with high yields. A preliminary mechanistic study to shed light into the reaction pathway was also carried out.
- Kumar, Rakesh,Kumar, Inder,Sharma, Ritika,Sharma, Upendra
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supporting information
p. 2613 - 2617
(2016/03/05)
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- Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN
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A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.
- Qiao, Kai,Wan, Li,Sun, Xiaoning,Zhang, Kai,Zhu, Ning,Li, Xin,Guo, Kai
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p. 1606 - 1611
(2016/04/05)
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- Synthesis of 2-Alkenylquinoline by Reductive Olefination of Quinoline N-Oxide under Metal-Free Conditions
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Synthesis of 2-alkenylquinoline by reductive olefination of quinoline N-oxide under metal-free conditions is disclosed. Practically, the reaction could be performed with quinoline as starting material via a one-pot, two-step process. A possible mechanism is proposed that involves a sequential 1,3-dipolar cycloaddition and acid-assisted ring opening followed by a dehydration process.
- Xia, Hong,Liu, Yuanhong,Zhao, Peng,Gou, Shaohua,Wang, Jun
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supporting information
p. 1796 - 1799
(2016/05/19)
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- Metal-Free, Phosphonium Salt-Mediated Sulfoximination of Azine N-Oxides: Approach for the Synthesis of N-Azine Sulfoximines
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Herein, we report a simple and metal-free method for the synthesis of N-azine sulfoximines by the nucleophilic substitution of azine N-oxides with NH-sulfoximines. The present method works at room temperature with wide functional group compatibility and gives several unprecedented N-azine sulfoximines. The reaction conditions were also found suitable with enantiopure substrates and furnished products without any racemization. It also finds an application in the sulfoximination of azine-based functional molecules such as 2,2′-bipyridine, 1,10-phenanthroline, and quinine.
- Aithagani, Sravan Kumar,Kumar, Mukesh,Yadav, Mahipal,Vishwakarma, Ram A.,Singh, Parvinder Pal
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p. 5886 - 5894
(2016/07/23)
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- Cu-Catalyzed Deoxygenative C2-Sulfonylation Reaction of Quinoline N-Oxides with Sodium Sulfinate
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An unexpected Cu-catalyzed deoxygenative C2-sulfonylation reaction of quinoline N-oxides in the presence of radical initiator K2S2O8 was developed that used sodium sulfinate as a sulfonyl coupling partner. The mechanism studies indicate that the reaction proceeds via Minisci-like radical coupling step to give sulfonylated quinoline with good chemical yields.
- Du, Bingnan,Qian, Ping,Wang, Yang,Mei, Haibo,Han, Jianlin,Pan, Yi
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supporting information
p. 4144 - 4147
(2016/08/30)
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- Copper-Catalyzed Regioselective Cascade Alkylation and Cyclocondensation of Quinoline N-Oxides with Diazo Esters: Direct Access to Conjugated π-Systems
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An inexpensive copper-catalyzed cascade regioselective alkylation, followed by cyclocondensation of quinoline N-oxides with α-diazo esters has been achieved successfully to provide heteroarene-containing conjugated π-systems. The developed method is simple, straightforward, and economical with a broad range of substrate scope. The dual role of copper catalyst in the C?H bond functionalization and in Lewis acid-promoted cyclization was explored.
- Biswas, Aniruddha,Karmakar, Ujjwal,Pal, Arun,Samanta, Rajarshi
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supporting information
p. 13826 - 13830
(2016/09/21)
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- Benzylation of heterocyclic N-oxides via direct oxidative cross-dehydrogenative coupling with toluene derivatives
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A novel cross-dehydrogenative coupling (CDC) of heterocyclic N-oxides with toluene derivatives has been discussed, allowing for the facile synthesis of a broad range of structurally diverse C1-benzyl quinoline N-oxides, isoquinoline N-oxides and pyridine N-oxides, including two methylated quinoline N-oxides in particular. This protocol not only extends the application of toluenes in synthetic organic chemistry, but also offers an alternative method to prepare benzylated heterocyclic N-oxides without any metal involved, which is important in medicinal chemistry.
- Wan,Qiao,Sun,Di,Fang,Li,Guo
-
supporting information
p. 10227 - 10232
(2016/12/07)
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- Regioselective Metal-Free Cross-Coupling of Quinoline N -Oxides with Boronic Acids
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A novel and operationally simple one-step C-H bond functionalization of quinoline N-oxides to 2-substituted quinolines was developed. This approach enables the regioselective functionalization under external oxidant- and metal-free conditions. The developed transformation represents the first application of the Petasis reaction in functionalization of heterocycles.
- Bering, Luis,Antonchick, Andrey P.
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supporting information
p. 3134 - 3137
(2015/06/30)
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- Insights into the mechanistic and synthetic aspects of the Mo/P-catalyzed oxidation of N-heterocycles
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A Mo/P catalytic system for an efficient gram-scale oxidation of a variety of nitrogen heterocycles to N-oxides with hydrogen peroxide as terminal oxidant has been investigated. Combined spectroscopic and crystallographic studies point to the tetranuclear Mo4P peroxo complex as one of the active catalytic species present in the solution. Based on this finding an optimized catalytic system has been developed. The utility and chemoselectivity of the catalytic system has been demonstrated by the synthesis of over 20 heterocyclic N-oxides.
- Larionov, Oleg V.,Stephens, David,Mfuh, Adelphe M.,Arman, Hadi D.,Naumova, Anastasia S.,Chavez, Gabriel,Skenderi, Behije
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p. 3026 - 3036
(2014/05/06)
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- Copper-catalyzed direct amination of quinoline N-oxides via C-H bond activation under mild conditions
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A highly efficient and concise one-pot strategy for the direct amination of quinoline N-oxides via copper-catalyzed dehydrogenative C-N coupling has been developed. The desired products were obtained in good to excellent yields for 22 examples starting from the parent aliphatic amines. This methodology provides a practical pathway to 2-aminoquinolines and features a simple system, high efficiency, environmental friendliness, low reaction temperature, and ligand, additives, base, and external oxidant free conditions.
- Zhu, Chongwei,Yi, Meiling,Wei, Donghui,Chen, Xuan,Wu, Yangjie,Cui, Xiuling
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supporting information
p. 1840 - 1843
(2014/05/06)
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- Regioselective bromination of fused heterocyclic N-oxides
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A mild method for the regioselective C2-bromination of fused azine N-oxides is presented, employing tosic anhydride as the activator and tetra-n-butylammonium bromide as the nucleophilic bromide source. The C2-brominated compounds are produced in moderate to excellent yields and with excellent regioselectivity in most cases. The potential extension of this method to other halogens, effecting C2-chlorination with Ts2O/TBACl is also presented. Finally, this method could be incorporated into a viable one-pot oxidation/bromination process, using methyltrioxorhenium/urea hydropgen peroxide as the oxidant.
- Wengryniuk, Sarah E.,Weickgenannt, Andreas,Reiher, Christopher,Strotman, Neil A.,Chen, Ke,Eastgate, Martin D.,Baran, Phil S.
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supporting information
p. 792 - 795
(2013/04/10)
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- Synthesis, photophysical and electrochemical properties of aza-boron-diquinomethene complexes
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A series of aza-boron-diquinomethene (aza-BODIQU) complexes with different aryl-substituents (B1-B6) were synthesized and characterized. Their photophysical properties were investigated systematically via spectroscopic and theoretical methods. All complexes exhibit strong 1π-π* absorption bands and intense fluorescent emission bands in the visible spectral region at room temperature. The fluorescence spectra in solution show the mirror image features of the S0→S1 absorption bands, which can be assigned to the 1π-π*/1ICT (intramolecular charge transfer) emitting states. Except for B6, all complexes exhibit high photoluminescence quantum yields (ΦPL = 0.47-0.93). The spectroscopic studies and theoretical calculations indicate that the photophysical properties of these aza-BODIQUs can be tuned by the appended aryl-substituents, which would be useful for rational design of boron-fluorine complexes with high emission quantum yield for organic light-emitting applications.
- Wang, Danfeng,Liu, Rui,Chen, Chen,Wang, Shifan,Chang, Jin,Wu, Chunhui,Zhu, Hongjun,Waclawik, Eric R.
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p. 240 - 249
(2013/10/21)
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- METALLOENZYME INHIBITOR COMPOUNDS
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The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.
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Page/Page column 55
(2012/05/19)
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- METALLOENZYME INHIBITOR COMPOUNDS
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The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.
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Page/Page column 65-67
(2012/05/31)
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- METALLOENZYME INHIBITOR COMPOUNDS
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The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.
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Page/Page column 23
(2012/06/18)
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- NOVEL INHIBITORS OF HEPATITIS C VIRUS REPLICATION
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The embodiments provide compounds of the general Formulae I, II, III, IV, or V as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.
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Page/Page column 269
(2011/07/06)
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- PHOSPHATIDYLINOSITOL 3 KINASE INHIBITORS
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Provided are compounds according to Formula (I), or stereoisomer, prodrug, polymorph, or pharmaceutically acceptable salt forms thereof, wherein X, Y, R1, R6 , R7, and R8 are as defined, which compounds are effective inhibitors of PI3-kinase and/or other medically and clinically relevant kinases. Also provided are pharmaceutical compositions and methods of using the compounds and compositions as PB -kinase and kinase inhibitors. More particularly, the compounds of the invention provide treatments and therapeutics for human diseases regulated by, or associated with, the activity of, PI3-kinases and/or protein kinases, or mutant or variant forms thereof.
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Page/Page column 132
(2010/01/12)
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- Bicyclo 4.4.0 antiviral derivatives
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This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with amido piperazine derivatives. These compounds possess unique antiviral activity
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Page/Page column 30
(2008/06/13)
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- IMIDAZO[4,5-B]QUINOLINE-DERIVATIVES AND THEIR USE AS NO-SYNTHASE INHIBITORS
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The compounds of formula I In which R1, R2, R3 and A have the meanings as given In the description are novel effective INOS Inhibitors.
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- KINETICS OF N-OXIDATION OF COMPOUNDS OF THE QUINOLINE SERIES AND ISOMERIC BENZOQUINOLINES BY PERBENZOIC ACID IN CHLOROFORM AND AQUEOUS DIOXANE
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The kinetics of the N-oxidation with perbenzoic acid of 15 derivatives of quinoline and benzoquinoline in chloroform and 19 compounds in 50percent aqueous dioxane at 20, 25, 30, and 35 deg C were subjected to a comparative study.The rate constants, parameters of Arrhenius equation, and the activation energies for the N-oxidation of the indicated monoazines were determined.A scale of the reactivities of derivatives of the quinoline series and benzoquinolines was calculated within the framework of general perturbation theory.
- Lokhov, R. E.
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