cas 396-30-5, 6-Fluoroquinoline | Articles data

Articles about 396-30-5Total 49 be found

Article title
Article abstract
Author
Journal number and time
Download

High efficiency microwave-assisted synthesis of quinoline from acrolein diethyl acetal and aniline utilizing Ni/Beta catalyst
A facile and solvent-free microwave-assisted approach to quinoline was developed by utilizing both acrolein diethyl acetal and aniline as reagents, firstly employing Ni/Beta zeolite as mild, ecofriendly and low-cost solid catalyst. As high as 83% yield of quinoline was quickly achieved at a short microwave time. The results indicated that the effect of Ni on Beta zeolite not only significantly promoted conversion of acrolein diethyl acetal to effective intermediate but also dramatically accelerated dehydrogenation rate of tetrahydroquinoline/dihydroquinoline to quinoline.
Li, An,Yang, Zan,Yang, Tao,Luo, Cai-Wu,Chao, Zi-Sheng,Zhou, Cong-Shan
p. 21 - 25
(2018)
Read Online

Dehydrogenation of N-Heterocyclic Compounds Using H2O2 and Mediated by Polar Solvents
The oxidative dehydrogenation of N-heterocyclic compounds by using H2O2 as oxidant in combination with polar solvents such as 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and H2O is described. Among these two solvents, the best yields for the heteroaromatic compounds were generally achieved in HFIP. However, it is remarkable, that the use of a non toxic solvent such as H2O gave such good yields. Furthermore, the procedure was implemented in larger-scale and HFIP was distilled from the reaction mixture and reused (up to 5 cycles) without a significant detriment in the reaction outcome. (Figure presented.).
Llopis, Natalia,Gisbert, Patricia,Baeza, Alejandro,Correa-Campillo, Jara
supporting information
p. 1205 - 1210
(2022/02/25)

Monomeric vanadium oxide: A very efficient species for promoting aerobic oxidative dehydrogenation of N-heterocycles
Monomeric active species are very interesting in heterogeneous catalysis. In this work, we proposed a method to prepare VOx-NbOy@C catalysts, which involve the one-pot hydrothermal synthesis of inorganic/organic hybrid materials containing V/Nb followed by thermal treatment under a reducing atmosphere. The prepared catalysts were characterized using different techniques, such as high-angle annular dark-field scanning transmission electron microscopy and X-ray absorption fine structure spectroscopy. It was shown that monomeric VOx species were dispersed homogeneously in the catalysts. The VOx-NbOy@C catalysts displayed high performance in the aerobic oxidative dehydrogenation of N-heterocycles to aromatic heterocycles. It was demonstrated that the selectivity of reaction over the catalyst with a very small amount of V (0.07 wt%) was much higher than that over the NbOy@C, and the catalyst also exhibited excellent stability in the reaction. The detailed study indicated that monomeric VO2 species were the most effective for promoting the reaction. This journal is
Xie, Zhenbing,Chen, Bingfeng,Zheng, Lirong,Peng, Fangfang,Liu, Huizhen,Han, Buxing
p. 431 - 437
(2021/01/11)

Geometric and electronic effects on the performance of a bifunctional Ru2P catalyst in the hydrogenation and acceptorless dehydrogenation of N-heteroarenes
The development of bifunctional catalysts for the efficient hydrogenation and acceptorless dehydrogenation of N-heterocycles is a challenge. In this study, Ru2P/AC effectively promoted reversible transformations between unsaturated and saturated N-heterocycles affording yields of 98% and 99%, respectively. Moreover, a remarkable enhancement in the reusability of Ru2P/AC was observed compared with other Ru-based catalysts. According to density functional theory calculations, the superior performance of Ru2P/AC was ascribed to specific synergistic factors, namely geometric and electronic effects induced by P. P greatly reduced the large Ru-Ru ensembles and finely modified the electronic structures, leading to a low reaction barrier and high desorption ability of the catalyst, further boosting the hydrogenation and acceptorless dehydrogenation processes.
Shao, Fangjun,Yao, Zihao,Gao, Yijing,Zhou, Qiang,Bao, Zhikang,Zhuang, Guilin,Zhong, Xing,Wu, Chuan,Wei, Zhongzhe,Wang, Jianguo
p. 1185 - 1194
(2021/02/16)

Method for realizing oxidative dehydrogenation of nitrogen-containing heterocyclic ring by using biomass-based carbon material
The invention provides a method for realizing oxidative dehydrogenation of a nitrogen-containing heterocyclic ring by using a biomass-based carbon material, and belongs to the field of organic synthesis. According to the method, the raw materials of the biomass-based carbon material comprise wheat, sorghum, rice, corn straw, wheat straw, peanut shells, sesame shells, bean shells and the like, and are crushed and then ground into powder, the powder is fully mixed with an inorganic alkali, and calcination is performed in an inert gas atmosphere to prepare the biomass-based carbon material; and by using air as an oxygen source, at a temperature of 50-120 DEG C, oxidative dehydrogenation of nitrogen-containing heterocyclic compounds to synthesize quinoline compounds, isoquinoline compounds, acridine compounds, quinazoline compounds, indole compounds, imine compounds, and even quinoline compounds with pharmaceutical activity can be achieved. According to the present invention, easily available wheat flour is adopted as a raw material to prepare a non-metal catalyst, the alkali is not added during the reaction process, and a remarkable industrial application prospect is achieved.
-
Paragraph 0010-0011; 0026-0027

(2021/06/26)

Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies
We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.
Lecroq, William,Schleinitz, Jules,Billoue, Mallaury,Perfetto, Anna,Gaumont, Annie-Claude,Lalevée, Jacques,Ciofini, Ilaria,Grimaud, Laurence,Lakhdar, Sami
p. 1237 - 1242
(2021/06/01)

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents
Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).
An, Ju Hyeon,Kim, Kyu Dong,Lee, Jun Hee
supporting information
p. 2876 - 2894
(2021/02/01)

Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions
Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is
Kim, Se Hyun,An, Ju Hyeon,Lee, Jun Hee
supporting information
p. 3735 - 3742
(2021/05/04)

NCP-Type Pincer Iridium Complexes Catalyzed Transfer-Dehydrogenation of Alkanes and Heterocycles?
A series of NCP-type pincer iridium complexes, (RNCCP)IrHCl (2a—2c) and (BQ-NCOP)IrHCl 3, have been studied for catalytic transfer alkane dehydrogenation. Complex 3 containing a rigid benzoquinoline backbone exhibits high activity and robustness in dehydrogenation of alkanes to form alkenes. Even more importantly, this catalyst system was also highly effective in the dehydrogenation of a wide range of heterocycles to furnish heteroarenes.
Wang, Yulei,Qian, Lu,Huang, Zhidao,Liu, Guixia,Huang, Zheng
supporting information
p. 837 - 841
(2020/05/18)

Catalytic Aerobic Dehydrogenatin of N-Heterocycles by N-Hydoxyphthalimide
Catalytic methods for the aerobic dehydrogenation of N-heterocycles are reported. In most cases, indoles are accessed efficiently from indolines using catalytic N-hydroxyphthalimide (NHPI) as the sole additive under air. Further studies revealed an improved catalytic system of NHPI and copper for the preparation of other heteroaromatics, for example quinolines. (Figure presented.).
Chen, Weidong,Tang, Hao,Wang, Weilin,Fu, Qiang,Luo, Junfei
supporting information
p. 3905 - 3911
(2020/08/10)

Method for preparation of quinoline compounds
The invention discloses a green preparation method of quinoline compounds. According to the method, cheap and easily available copper salt and N-hydroxyphthalimide are used as catalysts, oxygen is used as an oxidizing agent, oxidation of tetrahydroquinoline compounds is performed in an organic solvent, and synthesis of quinoline compounds is realized. The method has the advantages of simple reaction operation, low reaction cost, high yield, low metal pollution and the like.
-
Paragraph 0058-0060

(2020/11/12)

Superacid-promoted synthesis of quinoline derivatives
A series of vinylogous imines have been prepared from anilines and cinnamaldehydes. These substrates react in superacidic media to provide quinolines and related compounds. A mechanism for the conversion is proposed which involves the cyclization of dicationic superelectrophilic intermediates. Aromatization of the quinoline ring is thought to occur by superacid-promoted elimination of benzene.
Klumpp, Douglas A.,Stentzel, Michael R.,Vuong, Hein
supporting information

(2020/01/24)

Corrigendum: Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles (Chemistry - A European Journal, (2017), 23, 57, (14167-14172), 10.1002/chem.201703642)
The authors have been alerted to an error that was unfortunately missed at the time of publication. Table was duplicated with Table 4. The correct version of Table 2 is shown below. The authors apologise for any inconvenience caused. Organo-photoredox catalyzed oxidative dehydrogenation of tetrahydroquinolines (THQ).[a,b] (Table presented.) [a] Reaction conditions: 1 (0.5 mmol), rose bengal (1.0 mol %), N,N-dimethylacetamide (2.0 mL), open air atmosphere under visible-light irradiation at room temperature for 24 h. [b] Isolated yields. [c] 0.1 mol % of photoredox catalyst for 28 h.
Sahoo, Manoj K.,Jaiswal, Garima,Rana, Jagannath,Balaraman, Ekambaram
p. 7038 - 7038
(2019/05/17)

A Reusable Cobalt Catalyst for Reversible Acceptorless Dehydrogenation and Hydrogenation of N-Heterocycles
The development of robust catalytic systems based on base-metals for reversible acceptorless dehydrogenation (ADH) and hydrogenation of feedstock chemicals is very important in the context of ‘hydrogen storage’. Herein, we report a highly efficient reusable cobalt-based heterogeneous catalyst for reversible dehydrogenation and hydrogenation of N-heterocycles. Both the ADH and the hydrogenation processes operate under mild, benign conditions.
Jaiswal, Garima,Subaramanian, Murugan,Sahoo, Manoj K.,Balaraman, Ekambaram
p. 2449 - 2457
(2019/05/10)

Room temperature catalytic dehydrogenation of cyclic amines with the liberation of H2 using water as a solvent
Catalytic dehydrogenation of cyclic amines, in particular partially saturated N-heterocycles to N-heterocyclic arenes, with the removal of molecular hydrogen as the sole byproduct in water is reported. This dehydrogenation reaction proceeds smoothly under very mild and benign conditions and operates at room temperature. This distinctive reactivity has been achieved under dual catalytic conditions by merging the visible-light active [Ru(bpy)3]2+ as the photoredox catalyst and a newly synthesized cobalt complex as the proton-reduction catalyst. A detailed mechanistic study (control experiments, electrochemical studies, UV-visible experiments) is presented for the present dual catalysis.
Sahoo, Manoj K.,Balaraman, Ekambaram
supporting information
p. 2119 - 2128
(2019/04/26)

CONVERSION OF TETRAHYDROQUINOLINE DERIVATIVES TO QUINOLINE USING AZOCOMPOUND
The present invention relates to a method of converting tetrahydroquinoline derivatives into quinoline using an azo compound and, more specifically, to a conversion method which is performed in a deuterium chloroform (CDCl_3) or chloroform (CHCl_3) solution including dialkyl azodicarboxylate, which is a method of producing quinoline through a dehydrogenation reaction of 1,2,3,4-tetrahydroquinoline. According to the present invention, a dehydrogenation reaction rate is dependent on the electronic and steric properties of used dialkyl azodicarboxylate; and chloroform shows better results than other substances in solvents screened with diethyl azodicarboxylate. Various types of 1,2,3,4-tetrahydroquinoline undergo the dehydration reaction of the present invention to produce the corresponding quinoline in a yield of at least 90%; and diethyl hydrazo dicarboxylate, which is a reduced form of diethyl azodicarboxylate, is readily separated and recyclable.COPYRIGHT KIPO 2020
-
Paragraph 0041-0042; 0068; 0112-0116

(2020/03/10)

Efficient dehydrogenation of 1,2,3,4-tetrahydroquinolines mediated by dialkyl azodicarboxylates
Various dialkyl azodicarboxylates were investigated for the dehydrogenation of 1,2,3,4-tetrahydroquinolines to quinolines. The dehydrogenation rates varied according to the electronic and steric nature of the used dialkyl azodicarboxylates. Among solvents screened with diethyl azodicarboxylate, chloroform exhibited superior results to others. A variety of 1,2,3,4-tetrahydroquinolines underwent the present dehydrogenation to produce the corresponding quinolines. Diethyl hydrazodicarboxylate, which is a reduced species of diethyl azodicarboxylate, was easily separated for recycle.
Bang, Saet Byeol,Kim, Jinho
supporting information
p. 1291 - 1298
(2018/04/05)

Oxidation Potential Tunable Organic Molecules and Their Catalytic Application to Aerobic Dehydrogenation of Tetrahydroquinolines
In this work, oxidation potential tunable organic molecules, alkyl 2-phenyl hydrazocarboxylates, were disclosed. The exquisite tuning of their oxidation potentials facilitated a catalytic dehydrogenation of 1,2,3,4-tetrahydroquinolines in the presence of Mn(Pc) and O2.
Jung, Dahyeon,Jang, Seol Heui,Yim, Taeeun,Kim, Jinho
supporting information
p. 6436 - 6439
(2018/10/15)

Aerobic oxidative dehydrogenation of N-heterocycles catalyzed by cobalt porphyrin
An efficient catalytic procedure has been developed for the aerobic oxidative dehydrogenation of N-heterocycles by cobalt porphyrin in the absence of any additives. The catalytic system could tolerate various 1,2,3,4-tetrahydroquinoline derivatives and some other N-heterocycles. The corresponding N-heteroaromatics could be obtained in 59–86% yields. The mechanism investigation suggested that the aerobic oxidative dehydrogenation might proceed with imine intermediate through radical paths.
Zhou, Weiyou,Chen, Dongwei,Sun, Fu'an,Qian, Junfeng,He, Mingyang,Chen, Qun
supporting information
p. 949 - 953
(2018/02/09)

Visible-Light Photocatalyzed Deoxygenation of N-Heterocyclic N-Oxides
A scalable and operationally simple method is described that allows for the chemoselective deoxygenation of a wide range of N-heterocyclic N-oxides (a total of 36 examples). This visible-light-induced protocol features the use of only commercially available reagents, room-temperature conditions, and unprecedented chemoselective removal of the oxygen atom in a quinoline N-oxide in the presence of a pyridine N-oxide in the same molecule through the judicious selection of a photocatalyst.
Kim, Kyu Dong,Lee, Jun Hee
supporting information
p. 7712 - 7716
(2019/01/03)

Acceptorless Dehydrogenation of N-Heterocycles by Merging Visible-Light Photoredox Catalysis and Cobalt Catalysis
Herein, the first acceptorless dehydrogenation of tetrahydroquinolines (THQs), indolines, and other related N-heterocycles, by merging visible-light photoredox catalysis and cobalt catalysis at ambient temperature, is described. The potential applications to organic transformations and hydrogen-storage materials are demonstrated. Primary mechanistic investigations indicate that the catalytic cycle occurs predominantly by an oxidative quenching pathway.
He, Ke-Han,Tan, Fang-Fang,Zhou, Chao-Zheng,Zhou, Gui-Jiang,Yang, Xiao-Long,Li, Yang
supporting information
p. 3080 - 3084
(2017/03/14)

Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles
We report here for the first time the catalytic oxidative dehydrogenation of N-heterocycles by a visible-light organo-photoredox catalyst with low catalyst loading (0.1–1 mol %). The reaction proceeds efficiently under base- and additive-free conditions with ambient air at room temperature. The utility of this benign approach is demonstrated by the synthesis of various pharmaceutically relevant N-heteroarenes such as quinoline, quinoxaline, quinazoline, acridine, and indole.
Sahoo, Manoj K.,Jaiswal, Garima,Rana, Jagannath,Balaraman, Ekambaram
supporting information
p. 14167 - 14172
(2017/10/16)

Method for catalyzing nitrogen heterocyclic ring compound for oxidative dehydrogenation with hydrotalcite-like material
The invention relates to a method for catalyzing a nitrogen heterocyclic ring compound for oxidative dehydrogenation with a hydrotalcite-like material, and belongs to the application aspect of a hydrotalcite-like component. The hydrotalcite-like component can be expressed as: A-MxM-LDHs (A=OH or CO3; M=Ni, Co, Cu, Mg or Zn; M=Fe, Mn, Al; M/M=(2 to 4)). Under existence of the catalyst and without adding any additives, oxidative dehydrogenation reaction is performed on the heterocyclic ring compound under a mild condition to prepare a corresponding aromatic compound. According to the method provided by the invention, the hydrotalcite-like material is based on non-noble metal, can be synthesized largely, and can be recycled; the method has the advantages of being high in catalytic reaction efficiency, mild in reaction condition, low in cost, easy to industrialize and the like.
-
Paragraph 0048; 0049; 0050; 0051; 0052

(2017/10/27)

Cu-Catalyzed Aerobic Oxidation of Di-tert-butyl Hydrazodicarboxylate to Di-tert-butyl Azodicarboxylate and Its Application on Dehydrogenation of 1,2,3,4-Tetrahydroquinolines under Mild Conditions
A new class of co-catalytic system was developed with homogeneous CuI and di-tert-butyl azodicarboxylate for aerobic dehydrogenation of 1,2,3,4-tetrahydroquinolines under mild conditions. The developed co-catalytic system is consisting of di-tert-butyl azodicarboxylate-mediated dehydrogenation of 1,2,3,4-tetrahydroquinoline and aerobic oxidative regeneration of di-tert-butyl azodicarboxylate from di-tert-butyl hydrazodicarboxylate using molecular oxygen as a terminal oxidant. A variety of quinolines were efficiently synthesized by the developed Cu and di-tert-butyl azodicarboxylate co-catalytic system.
Jung, Dahyeon,Kim, Min Hye,Kim, Jinho
supporting information
p. 6300 - 6303
(2016/12/23)

Copper-Mediated Oxidative Fluorination of Aryl Stannanes with Fluoride
A regiospecific method for the oxidative fluorination of aryl stannanes using tetrabutylammonium triphenyldifluorosilicate (TBAT) and copper(II) triflate is described. This reaction is robust, uses readily available reagents, and proceeds via a stepwise protocol under mild conditions (60 °C, 3.2 h). Broad functional group tolerance, including arenes containing protic and nucleophilic groups, is demonstrated.
Gamache, Raymond F.,Waldmann, Christopher,Murphy, Jennifer M.
supporting information
p. 4522 - 4525
(2016/09/28)

Highly Enantioselective Direct Synthesis of Endocyclic Vicinal Diamines through Chiral Ru(diamine)-Catalyzed Hydrogenation of 2,2′-Bisquinoline Derivatives
An asymmetric hydrogenation of 2,2′-bisquinoline and bisquinoxaline derivatives, catalyzed by chiral cationic ruthenium diamine complexes, was developed. A broad range of chiral endocyclic vicinal diamines were obtained in high yields with excellent diastereo- and enantioselectivity (up to 93:7 dl/meso and >99 % ee). These chiral diamines could be easily transformed into a new class of chiral N-heterocyclic carbenes (NHCs), which are important but difficult to access.
Ma, Wenpeng,Zhang, Jianwei,Xu, Cong,Chen, Fei,He, Yan-Mei,Fan, Qing-Hua
supporting information
p. 12891 - 12894
(2016/10/04)

Catalytic Aerobic Dehydrogenation of Nitrogen Heterocycles Using Heterogeneous Cobalt Oxide Supported on Nitrogen-Doped Carbon
Dehydrogenation of (partially) saturated heterocycles provides an important route to heteroaromatic compounds. A heterogeneous cobalt oxide catalyst, previously employed for aerobic oxidation of alcohols and amines, is shown to be effective for aerobic dehydrogenation of various 1,2,3,4-tetrahydroquinolines to the corresponding quinolines. The reactions proceed in good yields under mild conditions. Other N-heterocycles are also successfully oxidized to their aromatic counterparts.
Iosub, Andrei V.,Stahl, Shannon S.
supporting information
p. 4404 - 4407
(2015/09/28)

HOTf-catalyzed intermolecular hydroamination reactions of alkenes and alkynes with anilines
Herein, the intermolecular hydroamination of alkenes and alkynes with anilines catalyzed by HOTf under mild conditions has been developed. This reaction provides one of the simplest alkene and alkyne addition methods and is an alternative to metal-catalyzed reactions. At the same time, the intramolecular hydroamination of alkynes with anilines proceeds smoothly to obtain quinolines. We found that this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.
Xu, Xuefeng,Zhang, Xu,Wang, Zhiqiang,Kong, Manman
p. 40950 - 40952
(2015/05/20)

Copper-catalyzed oxygen atom transfer of N-oxides leading to a facile deoxygenation procedure applicable to both heterocyclic and amine N-oxides
Deoxygenation of various types of N-oxides including both heterocyclic and alkyl(aryl)amine derivatives has successfully been developed by the copper-catalyzed oxygen atom transfer using diazo compounds as the oxygen acceptor. The reaction proceeds smoothly over a broad range of substrates with excellent functional group tolerance under mild conditions. This journal is
Jeong, Jisu,Lee, Donggun,Chang, Sukbok
supporting information
p. 7035 - 7038
(2015/04/22)

Silver-catalyzed oxidative coupling of aniline and ene carbonyl/acetylenic carbonyl compounds: An efficient route for the synthesis of quinolines
An efficient silver-mediated coupling of aniline with ene carbonyl/acetylenic carbonyl compounds for the synthesis of quinolines is reported. The transformation is effective for a broad range of substrates, thus enabling the expansion of substituent architectures on the heterocyclic framework. The electronic properties of the substituents on the amine have been investigated. It was found that molecules with both electron-donating and electron-withdrawing substituents were suitable substrates for this transformation, and the expected products were obtained in moderate to excellent yields. The use of a single catalytic system to mediate chemical transformations in a synthetic operation is important for the development of new atom-economic strategies and this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.
Zhang, Xu,Xu, Xuefeng
supporting information
p. 3089 - 3093
(2015/02/19)

Quinoline and phenanthroline preparation starting from glycerol via improved microwave-assisted modified Skraup reaction
An efficient "green" modified Skraup reaction in neat water was developed using inexpensive, abundant and environmentally-friendly glycerol under microwave irradiation conditions. Starting from aniline derivatives, various quinolines were obtained in 10-66% yields. The use of nitroaniline led to the corresponding phenanthrolines in 15-52% yields, respectively. This journal is the Partner Organisations 2014.
Saggadi, Hanen,Luart, Denis,Thiebault, Nicolas,Polaert, Isabelle,Estel, Lionel,Len
p. 21456 - 21464
(2014/06/10)

Cu(OTf)2-mediated fluorination of aryltrifluoroborates with potassium fluoride
This Communication describes the Cu(OTf)2-mediated fluorination of aryltrifluoroborates with KF. The reaction proceeds under mild conditions (at 60 C over 20 h) and shows a broad substrate scope and functional group tolerance. The Cu is proposed to play two separate roles in this transformation: (1) as a mediator for the aryl-F coupling and (2) as an oxidant for accessing a proposed CuIII(aryl)(F) intermediate.
Ye, Yingda,Schimler, Sydonie D.,Hanley, Patrick S.,Sanford, Melanie S.
supporting information
p. 16292 - 16295
(2013/12/04)

FLUORINATION OF ORGANIC COMPOUNDS
Methods for fluorinating organic compounds are described herein.
-
Page/Page column 24

(2012/11/06)

Mechanistic investigation of the nickel-catalyzed Suzuki reaction of N, O-acetals: Evidence for boronic acid assisted oxidative addition and an iminium activation pathway
The mechanism of a recently reported Suzuki coupling reaction of quinoline-derived allylic N,O-acetals has been studied using a combination of structural, stereochemical, and kinetic isotope effect experiments. The data indicate that C-O activation is fac
Sylvester, Kevin T.,Wu, Kevin,Doyle, Abigail G.
supporting information
p. 16967 - 16970,4
(2012/12/12)

Mechanistic investigation of the nickel-catalyzed Suzuki reaction of N, O-acetals: Evidence for boronic acid assisted oxidative addition and an iminium activation pathway
The mechanism of a recently reported Suzuki coupling reaction of quinoline-derived allylic N,O-acetals has been studied using a combination of structural, stereochemical, and kinetic isotope effect experiments. The data indicate that C-O activation is fac
Sylvester, Kevin T.,Wu, Kevin,Doyle, Abigail G.
supporting information
p. 16967 - 16970
(2013/01/15)

A novel improvement in ArLPdF catalytic fluorination of aromatic compounds
In this study, we used reverse micellar medium for overcoming the disadvantages of ArLMF catalytic fluorination of aromatic compounds. It not only enhanced the fluorination rate, but also widened the scope of reaction for bromoaromatics with electron donating and withdrawing functionalities at ortho position. Various bromoaromatic compounds were fluorinated using the biarylphosphine ligand i.e. cyclohexyl BrettPhos ligand, along with [cinnamylPdCl]2, and CsF as the fluoride source in reverse micellar media. The anisotropic palisade layer of reverse micelles provided the active site for reaction. The most crucial factor in the critical reductive elimination step could be the spatial orientation of ArLPdF complex in the palisade layer; forming ArF as the final product in high yield with excellent selectivity.
Samant, Bhupesh S.,Bhagwat, Sunil S.
experimental part
p. 191 - 194
(2012/01/05)

Deoxyfluorination of phenols
An operationally simple ipso fluorination of phenols with a new deoxyfluorination reagent is presented.
Tang, Pingping,Wang, Weike,Ritter, Tobias
supporting information; experimental part
p. 11482 - 11484
(2011/10/02)

Silver-mediated fluorination of aryl silanes
A regiospecific silver-mediated fluorination of aryl silanes is reported. The reaction is operationally simple, and employs Ag2O as readily available, inexpensive silver source, which can be recovered.
Tang, Pingping,Ritter, Tobias
supporting information; experimental part
p. 4449 - 4454
(2011/08/03)

FLUORINATION OF ORGANIC COMPOUNDS
Methods for fluorinating organic compounds are described herein.
-
Page/Page column 65; 96; 108

(2010/07/10)

COMPOUND HAVING 11 ?-HSD1 INHIBITORY ACTIVITY
The present invention provides compounds having excellent 11β-HSD1 inhibitory activity. A compound represented by the following formula (I): [wherein X1 represents an oxygen atom, or the formula -(CR11R12)p-, etc., Y1 represents a hydrogen atom, a hydroxyl group, etc., Z1 represents an oxygen atom or the formula -(NR14)-, R1 represents a hydrogen atom, a halogen atom, a cyano group, a C1-4 alkyl group, a C1-4 alkyl group substituted with 1 to 3 halogen atoms, a C1-4 alkoxy group, a C1-4 alkoxycarbonyl group, a carboxyl group, a carbamoyl group, or an amino group, and m represents an integer of 1 or 2, and R2 represents a hydrogen atom or a C1-4 alkyl group, and n represents an integer of 1 or 2].
-
Page/Page column 10

(2010/04/25)

Fluorination of boronic acids mediated by silver(I) Triflate
A regiospecific Ag-mediated fluorination reaction of aryl- and alkenylboronic acids and esters Is reported. The fluorination reaction uses commercially available reagents, does not require the addition of exogenous ligands, and can be performed on a multigram scale. This report discloses the first practical reaction sequence from arylboronic acid to aryl fluorides.
Furuya, Takeru,Ritter, Toblas
supporting information; experimental part
p. 2860 - 2863
(2009/12/05)

Formation of arf from lpdar(f): catalytic conversion of aryl triflates to aryl fluorides
Despite increasing pharmaceutical importance, fluorinated aromatic organic molecules remain difficult to synthesize. Present methods require either harsh reaction conditions or highly specialized reagents, making the preparation of complex fluoroarenes ch
Watson, Donald A.,Su, Mingjuan,Teverovskiy, Georgiy,Zhang, Yong,Garcia-Fortanet, Jorge,Kinzel, Tom,Buchwaldf, Stephen L.
scheme or table
p. 1661 - 1664
(2010/06/16)

Silver-mediated fluorination of functionalized aryl stannaries
-
Furuya, Takeru,Strom, Alexandra E.,Ritter, Tobias
supporting information; experimental part
p. 1662 - 1663
(2009/07/25)

RENIN INHIBITORS
The present invention relates to novel renin inhibitors of general formula (1), novel intermediates involved in their synthesis, their pharmaceutically acceptable salts and pharmaceutical compositions containing them. The present invention also relates to a process of preparing compounds of general formula (1), their tautomeric forms, their pharmaceutically acceptable salts, pharmaceutical compositions containing them, and novel intermediates involved in their synthesis.
-
Page/Page column 24

(2009/09/04)

ANTIDEPRESSANT ARYLPIPERAZINE DERIVATIVES OF HETEROCYCLE-FUSED BENZODIOXANS
Compounds of the formula I: are useful for the treatment of depression (including but not limited to major depressive disorder, childhood depression and dysthymia), anxiety, panic disorder, post-traumatic stress disorder, premenstrual dysphoric disorder (also known as pre-menstrual syndrome), attention deficit disorder (with and without hyperactivity), obsessive-compulsive disorder, social anxiety disorder, generalized anxiety disorder, obesity eating disorders such as anorexia nervosa and bulimia nervosa, vasomotor flushing, cocaine and alcohol addiction, sexual dysfunction and related illnesses.
-
Page 61-62

(2008/06/13)

13C NMR studies on the structure of 5H- and 6H-indolo-[2,3-b] quinolines and the related compounds
A set of 13C NMR data which included one-bond spin-spin coupling constants has been obtained for a large series of heteroaromatic compounds. It contains, among others, 6-substituted quinolines, their N-oxides, 2- and 5-methoxyindoles. The results obtained for these basic molecules were compared with those measured for a series of variously substituted 5H- and 6H-indolo[2,3-b]quinolines, which shed new light on the electronic structure of the two latter groups of the compounds.
Kamieńska-Trela,Kania,Bechcicka,Kaczmarek
p. 209 - 218
(2007/10/03)

Selective direct fluorination of quinoline derivatives
Direct fluorination of various quinoline derivatives in acidic reaction media gives fluorinated quinoline products arising from selective, efficient electrophilic substitution processes.
Chambers, Richard D,Holling, Darren,Sandford, Graham,Puschmann, Horst,Howard, Judith A.K
p. 99 - 101
(2007/10/03)

Synthesis of quinolines via ortho-lithiated N-acylanilines. A modified Friedlander synthesis
-
Cho,Gong,Muchowski
p. 7288 - 7291
(2007/10/02)

Amino-substituted imidazo[1,2-a:3,4-a']diquinolin-15-ium salts compositions and method of use
Amino-substituted imidazo[1,2-a:3,4-a']diquinolin-15-ium salts having the formula I: STR1 wherein R1 is hydrogen, lower alkyl, C4 -C6 cycloalkyl, di(lower alkyl)amino, 1-azetidinyl, 1-pyrrolidinyl, 1-piperidinyl, methyl-1-pyrrolidinyl, methyl-1-piperidinyl, 4-morpholinyl or 2,2-dimethylhydrazino; R2 is hydrogen, lower alkyl, lower alkylamino, di(lower alkyl)amino, C4 -C6 cycloalkylamino, lower alkoxy(lower alkyl)amino, 1-azetidinyl, 1-pyrrolidinyl, 1-piperidinyl, methyl-1-pyrrolidinyl, methyl-1-piperidinyl, hexahydro-1H-azepin-1-yl, 4-morpholinyl, benzylamino, N-methylbenzylamino or 2-phenylethylamino; R3 is hydrogen or methyl; X is an anion; with the proviso that at least one of R1 and R2 is other than hydrogen, lower alkyl or C4 -C6 cycloalkyl; and with the further proviso that when R2 is dimethylamino, at least one of R1 and R3 is other than hydrogen, and intermediates used in the preparation thereof are disclosed. The compounds of the invention are prepared by amination of the corresponding chloro or fluoro-substituted imidazo [1,2-a:3,4-a']diquinolin-15-ium salts; either the halo substituted intermediates or the amino substituted salts may be further treated, typically using ion exchange techniques to obtain a variety of physiologically acceptable amino-substituted [1,2-a:3,4-a']diquinolin-15-ium salts which exhibit antifungal activity.
-
(2008/06/13)