- The synthesis and characterisation of coordination and hydrogen-bonded networks based on 4-(3,5-dimethyl-1H-pyrazol-4-yl)benzoic acid
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The synthesis, structural and thermal characterisation of a number of coordination complexes featuring the N,O-heteroditopic ligand 4-(3,5-dimethyl-1H-pyrazol-4-yl)benzoate, HL are reported. The reaction of H2L with cobalt(II) and nickel(II) ni
- Bryant, MacGuire R.,Burrows, Andrew D.,Fitchett, Christopher M.,Hawes, Chris S.,Hunter, Sally O.,Keenan, Luke L.,Kelly, David J.,Kruger, Paul E.,Mahon, Mary F.,Richardson, Christopher
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Read Online
- Vitamin B1-catalyzed aerobic oxidative esterification of aromatic aldehydes with alcohols
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A straightforward aerobic oxidative esterification of aryl aldehydes with alcohols has been developed for the synthesis of substituted esters by employing vitamin B1 as a cost-effective, metal-free, and eco-friendly NHC catalyst. Air is used as a green terminal oxidant. The reaction is a useful addition to the existing NHC-catalytic oxidative esterification.
- Chu, Xue-Qiang,Ge, Danhua,Luo, Xin-Long,Xu, Pei,Yu, Zi-Lun
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supporting information
p. 30937 - 30942
(2021/11/19)
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- Access to α,α-Difluoro-γ-amino Acids by Nickel-Catalyzed Reductive Aryldifluoroacetylation of N -Vinylacetamide
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A nickel-catalyzed reductive aryldifluoroacetylation of N -vinylacetamide with ethyl chloro(difluoro)acetate and aryl iodides is described. This chelating amide carbonyl group-assisted strategy provides rapid access to a variety of protected α,α-difluoro-γ-amino acids that might have potential applications in peptide chemistry and protein engineering. An advantage of this method is its synthetic simplicity, with no preparation of organometallic reagents.
- Zhao, Qing-Wei,Yang, Zhi-Fang,Fu, Xia-Ping,Zhang, Xingang
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supporting information
p. 1565 - 1569
(2020/11/16)
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- Green synthesis of zinc oxide particles with apple-derived compounds and their application as catalysts in the transesterification of methyl benzoates
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ZnO nanoparticles (ZnONPs) were successfully synthesized using bravo-de-esmolfe apple extract in aqueous medium at room temperature. ZnO microparticles, prepared with a pure apple phytochemical, quercetin (ZnOq), or without phytochemicals (ZnO) were studied for comparative purposes. The re-use of apple waste for highly efficient catalyst production, based on green synthetic routes, can be added to the concept of a circular economy. The synthesized ZnO particles were characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and N2adsorption/desorption Brunauer-Emmett-Teller (BET) theory. The XRD patterns indicated the formation of a hexagonal wurtzite phase with high purity and SEM and TEM analyses revealed the morphology of the particles. The apple extract produced spherical ZnONPs composed of round lamina-like structures, similar to the micro sized lamina-like shape of ZnOq and dissimilar to the flower-like shape of ZnO. The green synthesized ZnO nanoparticles (ZnONPs) led to a high product yield ofca. 96% within 24 h of reaction time in the transesterification reaction of different carboxylic esters.
- Alegria, Elisabete C. B. A.,Alves, Marta M.,Fátima Montemor, M.,Pombeiro, Armando J. L.,Ribeiro, Ana P. C.,Saraiva, Marta S.,Soliman, Mohamed M. A.
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p. 6488 - 6494
(2020/06/03)
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- Construction of Esters through Sulfuryl Fluoride (SO 2 F 2) Mediated Dehydrative Coupling of Carboxylic Acids with Alcohols at Room Temperature
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A facile method for the construction of esters through dehydrative coupling of carboxylic acids with alcohols is developed. The reactions are mediated by sulfuryl fluoride (SO 2 F 2) at room temperature and proceed with high efficiency. The method has several advantages including broad substrate scope, mild conditions, excellent functional group compatibility and affords high yields, even on gram scale.
- Qin, Hua-Li,S Alharbi, Njud,Wang, Shi-Meng
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p. 3901 - 3907
(2019/10/11)
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- Fluoroboron pyrrole liquid crystal compound containing 8-(diphenylethinyl)-ester group flexible multi-element rings, preparation method and application thereof
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The invention relates to fluoroboron pyrrole liquid crystal dye containing 8-(diphenylethinyl)-ester group flexible multi-element rings, a preparation method and application thereof. According to theinvention, boron fluoride complex dipyrrole methine is used as a matrix, a diphenylacetylene rigid structure is introduced into a No. 8 position through a Sonogashira coupling reaction, a series of BODIPY-type dichroic dye of the 8-methyl-(diphenylethinyl)-ester group flexible multi-element rings is designed and synthetized by connecting bicyclohexyl, cholesterol and other flexible multi-element rings with a diphenyl acetenyl group through an esterification reaction. The maximum emission wavelength of the compound in dichloromethane is all concentrated at about 525nm, so that the compound presents green fluorescence, and a good dichroic ratio and ordered parameters are shown in liquid crystal E7; the liquid crystal compound has a liquid crystal intermediate phase in the temperature range of 100-280 DEG C, and can be used for manufacturing liquid crystal display products, particularly, the liquid crystal compound is used as a guest dye for a guest host mode liquid crystal display; whenthe compound is added to E7 liquid crystal and used in a guest host display mode, the response time can be improved, and the effect of quick response can be achieved.
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Paragraph 0045; 0047-0049
(2019/06/27)
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- Synthesis and bioactivity of sulfide derivatives containing 1,3,4-oxadiazole and pyridine
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A series of novel sulfide derivatives containing 1,3,4-oxadiazole and pyridine were synthesized, characterized, and tested for their antibacterial activity against tobacco bacterial wilt and rice bacterial blight and for insecticidal activity toward diamondback moth. The results showed that some compounds had good insecticidal and bactericidal activity, e.g., the activities of compounds 6e and 6g–6j toward tobacco bacterial wilt were much better than those of commercial thiodiazole-copper, and some of the synthesized compounds possessed good insecticidal activity against Plutella xylostella. Compounds 6d, 6h, 6j, 6l, 6p, 6r, and 6p displayed over 93% activity at 500 mg L? 1.
- Yu, Gang,Chen, Shunhong,He, Feng,Luo, Dexia,Zhang, Yu,Wu, Jian
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p. 1075 - 1085
(2019/09/10)
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- ZnO nanoparticles: An efficient catalyst for transesterification reaction of α-keto carboxylic esters
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Pure ZnO nanoparticles were synthesized by a sustainable precipitation method using zinc nitrate and sodium hydroxide in aqueous medium at room temperature. They were characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM-EDX), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FTIR), ultraviolet-visible spectroscopy (UV–vis) spectroscopy and Brunauer-Emmett-Teller (BET) analysis. The XRD patterns indicate the formation of the hexagonal wurtzite phase with high purity and SEM-EDS analysis confirm the purity and a homogenous distribution of the nanostructures. The ZnO nanostructures present plate-like agglomerates, resulting in a quasi-spherical morphology. The catalytic activity of the formed ZnO nanoparticles was evaluated towards the transesterification reaction of different carboxylic esters in the presence of various alcohols. This catalyst is highly selective for the transesterification of α-keto carboxylic ester (methyl benzoylformate) and leads to ca. 97percent of product yield within 24 h of reaction time.
- Alegria, Elisabete C. B. A.,Karmakar, Anirban,Pombeiro, Armando J. L.,Rúbio, Guilherme M. D. M.,Ribeir, Ana P. C.,Saraiva, Marta S.,Soliman, Mohamed M. A.,da Silva, M. Fátima C. Guedes
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- Direct Pd(II)-Catalyzed Site-Selective C5-Arylation of 2-Pyridone Using Aryl Iodides
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A straightforward Pd(II)-catalyzed general strategy was developed for the C5-selective arylation of the 2-pyridone core with easily available aryl iodides. The transformation was highly regioselective and accomplished with a wide scope and functional group tolerance. Silver nitrate played a crucial role in this direct site-selective arylation. The method was extended to synthesize biologically active molecules.
- Maity, Saurabh,Das, Debapratim,Sarkar, Souradip,Samanta, Rajarshi
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supporting information
p. 5167 - 5171
(2018/09/13)
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- A general electrochemical strategy for the Sandmeyer reaction
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Herein we report a general electrochemical strategy for the Sandmeyer reaction. Using electricity as the driving force, this protocol employs a simple and inexpensive halogen source, such as NBS, CBrCl3, CH2I2, CCl4, LiCl and NaBr for the halogenation of aryl diazonium salts. In addition, we found that these electrochemical reactions could be performed using anilines as the starting material in a one-pot fashion. Furthermore, the practicality of this process was demonstrated in the multigram scale synthesis of aryl halides using highly inexpensive graphite as the electrode. A series of detailed mechanism studies have been performed, including radical clock and radical scavenger study, cyclic voltammetry analysis and in situ electron paramagnetic resonance (EPR) analysis.
- Liu, Qianyi,Sun, Beiqi,Liu, Zheng,Kao, Yi,Dong, Bo-Wei,Jiang, Shang-Da,Li, Feng,Liu, Guoquan,Yang, Yang,Mo, Fanyang
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p. 8731 - 8737
(2018/12/10)
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- Design, synthesis, insecticidal activity and 3D-QSR study for novel trifluoromethyl pyridine derivatives containing an 1,3,4-oxadiazole moiety
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A series of trifluoromethyl pyridine derivatives containing 1,3,4-oxadiazole moiety was designed, synthesized and bio-assayed for their insecticidal activity. The result of bio-assays indicated the synthesized compounds exhibited good insecticidal activity against Mythimna separata and Plutella xylostella, most of the title compounds show 100% insecticidal activity at 500 mg L-1 and >80% activity at 250 mg L-1 against the two pests. Compounds E18 and E27 showed LC50 values of 38.5 and 30.8 mg L-1 against Mythimna separata, respectively, which were close to that of avermectin (29.6 mg L-1); compounds E5, E6, E9, E10, E15, E25, E26, and E27 showed 100% activity at 250 mg L-1, which were better than chlorpyrifos (87%). CoMFA and CoMSIA models with good predictability were proposed, which revealed the electron-withdrawing groups with an appropriate bulk at 2- and 4-positions of benzene ring could enhance insecticidal activity.
- Xu,Wang,Luo,Yu,Guo,Fu,Zhao,Wu
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p. 6306 - 6314
(2018/02/19)
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- Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes
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Radiopharmaceuticals that incorporate radioactive iodine in combination with single-photon emission computed tomography imaging play a key role in nuclear medicine, with applications in drug development and disease diagnosis. Despite this importance, there are relatively few general methods for the incorporation of radioiodine into small molecules. This work reports a rapid air- and moisture-stable ipso-iododeboronation procedure that uses NIS in the non-toxic, green solvent dimethyl carbonate. The fast reaction and mild conditions of the gold-catalysed method led to the development of a highly efficient process for the radiolabelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selective radiosynthesis. This was exemplified by the efficient synthesis of radiolabelled meta-[125I]iodobenzylguanidine, a radiopharmaceutical that is used for the imaging and therapy of human norepinephrine transporter-expressing tumours.
- Webster, Stacey,O'Rourke, Kerry M.,Fletcher, Conor,Pimlott, Sally L.,Sutherland, Andrew,Lee, Ai-Lan
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supporting information
p. 937 - 943
(2017/12/26)
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- One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides
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A metal-free synthesis of aryl bromides and iodides from anilines via halogen abstraction from bromotrichloromethane and diiodomethane is described. This one-pot reaction affords aryl halides from the corresponding anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. DFT calculations support a SRN1 mechanism. This method represents a convenient alternative to the classic Sandmeyer reaction.
- Leas, Derek A.,Dong, Yuxiang,Vennerstrom, Jonathan L.,Stack, Douglas E.
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supporting information
p. 2518 - 2521
(2017/05/24)
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- A 4 - carboxyl preparation process of boric acid (by machine translation)
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The invention discloses a 4 - carboxyl boric acid process. In order to to iodine benzoic acid as the raw material, by esterification reaction, sediment reaction and hydrolysis reaction to obtain the target product 4 - carboxyl boric acid, the total yield can reach 88.7%. The process route raw materials are cheap and easy to obtain, after-treatment is convenient, high yield, easy industrialized application. (by machine translation)
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Paragraph 0029; 0030; 0053; 0054; 0069; 0070
(2017/08/28)
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- Graphene Oxide: An Efficient Acid Catalyst for the Construction of Esters from Acids and Alcohols
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Graphene oxide was found to be an efficient and reusable acid catalyst for the esterification reaction. A wide range of aliphatic and aromatic acids and alcohols were compatible with the standard conditions and afforded the corresponding products in good yields. The heterogeneous catalyst can be easily recovered and recycled in dichloro-ethane solvent with good catalytic activity.
- Chen, Zhengwang,Wen, Yuelu,Fu, Yejuan,Chen, Hai,Ye, Min,Luo, Guotian
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supporting information
p. 981 - 985
(2017/05/05)
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- Zinc Complexes with Cyanoxime: Structural, Spectroscopic, and Catalysis Studies in the Pivaloylcyanoxime-Zn System
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Reaction of 2-hydroxyimino-4,4-dimethyl-3-oxo-pentanenitrile (common abbreviation HPiCO, pivaloyl-cyanoxime) with zinc sulfate in an aqueous solution results in the formation of the two new complexes: [Zn(PiCO){H(PiCO)2}(H2O)] (I) and tetranuclear Zn complex [Zn4(μ3-OH)2(PiCO)6 (H2O)4] (II). Both complexes were characterized by elemental analysis, IR- and UV-visible spectra, DSC/TGA studies, and X-ray analysis. In complex II, the PiCO- cyanoxime anion adopts three bidentate binding modes: O-monodentate, chelating (κ2), and bridging (2) coordinations. Also, the ligand represents the mixture of two diasteromers (cis-anti and cis-syn) that form five- and six-membered chelate rings with Zn atoms and cocrystallize in one unit cell at population of 0.57-0.43. There are two crystallographically different Zn-centers in the ASU, and two μ3-bridging hydroxo-groups arrange via inversion center the formation of an elegant tetranuclear complex. Each Zn atom has a molecule of coordinated water and is in the distorted octahedral environment. Because of the structural flexibility and multidentate propensity of the pivaloyl-cyanoxime, complex II may act as a structural model of naturally occurring Zn-containing enzymes. Indeed, compound I exhibits an efficient catalytic performance for transesterification reaction of various esters in ethanol under mild reaction conditions. Therefore, obtained results allow assignment of observed activity as green catalysis.
- Opalade, Adedamola A.,Karmakar, Anirban,Rúbio,Pombeiro, Armando J. L.,Gerasimchuk, Nikolay
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p. 13962 - 13974
(2017/11/24)
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- Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature
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Despite the wide use of aryl radicals in organic synthesis, current methods to prepare them from aryl halides, carboxylic acids, boronic acids, and diazonium salts suffer from limitations. Aryl triflates, easily obtained from phenols, are promising aryl radical progenitors but remain elusive in this regard. Inspired by the single electron transfer process for aryl halides to access aryl radicals, we developed a simple and efficient protocol to convert aryl triflates to aryl radicals. Our success lies in exploiting sodium iodide as the soft electron donor assisted by light. This strategy enables the scalable synthesis of two types of important organic molecules, i.e., aryl boronates and aryl iodides, in good to high yields, with broad functional group compatibility in a transition-metal-free manner at room temperature. This protocol is anticipated to find potential applications in other aryl-radical-involved reactions by using aryl triflates as aryl radical precursors.
- Liu, Wenbo,Yang, Xiaobo,Gao, Yang,Li, Chao-Jun
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supporting information
p. 8621 - 8627
(2017/07/06)
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- Copper-catalysed aromatic-Finkelstein reactions with amine-based ligand systems
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A new efficient and low-cost ligand, diethylenetriamine, has been utilised to promote the iodination of 16 different bromo-substrates via the copper catalysed Finkelstein halogen exchange reaction under mild conditions. In contrast to earlier methods, the use of inert atmosphere conditions was not required to obtain high yields and purity. Studies on the speciation of the catalyst in solution indicate rapid disproportionation of copper(i) in the presence of diethylenetriamine to give copper(0) and a bis-ligated copper(ii) complex which is characterised by X-ray diffraction. This copper(ii) complex was also shown to be catalytically active in the halogen exchange reaction. In contrast, no significant disproportionation was observed using dimethylethylenediamine as the ligand, and the solid-state structures of a copper(i) dimeric complex and a 2D polymeric network of copper(i) iodide tetramers are reported. The catalytic activity of diethylenetriamine and dimethylethylenediamine with both copper(i) and copper(ii) salts are compared, and possible mechanistic implications discussed.
- Jin, Xiaodong,Davies, Robert P.
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p. 2110 - 2117
(2017/07/22)
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- EXPANSION OF RENEWABLE STEM CELL POPULATIONS
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Ex vivo and in vivo methods of expansion of renewable stem cells, expanded populations of renewable stem cells and their uses.
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Paragraph 0438
(2016/05/02)
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- Diarylthiophenes as inhibitors of the pore-forming protein perforin
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Evolution from a furan-containing high-throughput screen (HTS) hit (1) resulted in isobenzofuran-1(3H)-one (2) as a potent inhibitor of the function of both isolated perforin protein and perforin delivered in situ by intact KHYG-1 NK cells. In the current study, structure-activity relationship (SAR) development towards a novel series of diarylthiophene analogues has continued through the use of substituted-benzene and -pyridyl moieties as bioisosteres for 2-thioxoimidazolidin-4-one (A) on a thiophene (B) -isobenzofuranone (C) scaffold. The resulting compounds were tested for their ability to inhibit perforin lytic activity in vitro. Carboxamide (23) shows a 4-fold increase(2) in lytic activity against isolated perforin and provides good rationale for continued development within this class.
- Miller, Christian K.,Huttunen, Kristiina M.,Denny, William A.,Jaiswal, Jagdish K.,Ciccone, Annette,Browne, Kylie A.,Trapani, Joseph A.,Spicer, Julie A.
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p. 355 - 360
(2016/01/09)
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- Rhodium-Catalyzed Double Alkyl-Oxygen Bond Cleavage: An Alkyl Transfer Reaction from Bis/Tris(o-alkyloxyphenyl)phosphine to Aryl Acids
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An unprecedented rhodium-catalyzed selective cleavage of double alkyl-oxygen bonds of bis/tris(o-alkyloxyphenyl)phosphine has been realized, in which P atom functions as a directing group and simple aryl acids are the methyl group acceptor to provide methyl esters and a quaternary phosphonium salt. The preliminary mechanism was investigated via an 18O labeling experiment and stoichiometric reaction between a Rh-A crystal and an aromatic acid.
- Zhou, Hui,Zhang, Jinlong,Yang, Huameng,Xia, Chungu,Jiang, Gaoxi
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supporting information
p. 3406 - 3412
(2016/10/21)
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- Copper-catalyzed conversion of aryl and heteroaryl bromides into the corresponding iodide
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An efficient method for the synthesis of aryl and heteroaryl iodides is described in this study. The reactions of aryl and heteroaryl bromides with potassium iodide proceeded smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding iodides in satisfactory to excellent yields.
- Feng, Xiujuan,Li, Lingyu,Yu, Xiaoqiang,Yamamoto, Yoshinori,Bao, Ming
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p. 129 - 132
(2016/07/06)
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- Copper-mediated aerobic iodination and perfluoroalkylation of boronic acids with (CF3)2CFI at room temperature
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The copper-mediated aerobic reactions between the branched (CF3)2CFI and boronic acids (R-B(OH)2) are described. Different from the linear perfluoroalkyl analogs CF3(CF2)nI (n?=?2, 3, 5, 7), (CF3)2CFI reacting with R-B(OH)2at room temperature under air in the presence of catalytic Cu powder provided exclusively the corresponding iodides (R-I), while the aerobic reactions of arylboronic acids with (CF3)2CFI at room temperature in the presence of Cu(OAc)2gave the perfluoroalkylation products (R-CF(CF3)2) in acceptable to moderate yields. The iodination reaction could be further promoted by hydroquinone, the addition of which improved the oxidation ability of (CF3)2CFI and provided the ipso-iodination products in high yields. The perfluoroalkylation was facilitated by the copper carboxylates since the addition of these salts into the reaction mixtures could successfully give rise to Ar-CF(CF3)2.
- Liu, Xi-Hai,Leng, Jing,Jia, Su-Jiao,Hao, Jian-Hong,Zhang, Fanglin,Qin, Hua-Li,Zhang, Cheng-Pan
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- Synthesis of novel triazoles and a tetrazole of escitalopram as cholinesterase inhibitors
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A novel serie of escitalopram triazoles (60-88) and a tetrazole (89) have been synthesized and subjected to a study to establish the inhibitory potential of these compounds toward acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Some selectivity in inhibition has been observed. The 4-chlorophenyl- (75, IC50, 6.71 ± 0.25 μM) and 2-methylphenyl- (70, IC50, 9.52 ± 0.23 μM) escitalopram triazole derivatives depicted high AChE inhibition, while 2-fluorophenyl- (76, IC50 = 4.52 ± 0.17 μM) and 4-fluorophenyl- (78, IC50 = 5.31 ± 0.43 μM) have found to be excellent BChE inhibitors. It has also been observed that ortho, meta and para substituted electron donating groups increase the inhibition, while electron withdrawing groups reduce the inhibition. Docking analyses of inhibitors with AChE have depicted the binding energies for 70 and 75 as ΔGbind -6.42 and -6.93 kcal/mol, respectively, while ligands 76 and 78 have shown the binding affinity ΔGbind -9.04 and -8.51 kcal/mol, respectively, for BChE.
- Mehr-Un-Nisa,Munawar, Munawar A.,Chattha, Fauzia A.,Kousar, Samina,Munir, Jawaria,Ismail, Tayaba,Ashraf, Muhammad,Khan, Misbahul A.
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p. 6014 - 6024
(2015/11/11)
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- Chemistry and antioxidant properties of titanium(IV) complexes
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Abstract The synthesis of titanium(IV) complexes with biologically active hydrazide ligands has been carried out. The complexes were characterized by spectroscopic methods (IR, 1H NMR and 13C NMR), elemental analysis and conductivity studies. These studies suggest bidentate coordination of the ligands through carbonyl oxygen and primary amine nitrogen, resulting in octahedral geometries. Hydrazides with pyridyl substituents displayed 1:2 metal-to-ligand ratio, and hydrazides with imino substituents exhibited 1:3 metal-to-ligand ratio resulting in an outer sphere complex. The remaining complexes displayed inner sphere coordination with 1:1 metal-to-ligand ratio. These complexes exhibit varying degrees of radical scavenging properties against DPPH, superoxide and nitric oxide free radicals. The free ligands showed inhibition against DPPH but were inactive against superoxide and nitric oxide free radicals. The structure-activity relationships of the complexes are discussed.
- Shaikh, Zara,Ashiq, Uzma,Jamal, Rifat Ara,Mahroof-Tahir, Mohammad,Shamshad, Bushra,Sultan, Sadaf
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p. 665 - 671
(2015/08/06)
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- A practical and general ipso iodination of arylboronic acids using N-iodomorpholinium iodide (NIMI) as a novel iodinating agent: mild and regioselective synthesis of aryliodides
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A mild and efficient protocol for the ipso-iodination of aryl boronic acids using N-iodomorpholinium iodide (NIMI) generated in situ from morpholine and molecular iodine as a novel iodinating agent has been developed. The addition of a catalytic amount of copper iodide found to promote rate enhancement of the iodination reaction and dramatic increase in the yield depending upon the nature of the boronic acid was observed. The mechanistic study revealed that depending upon the nature of the substrate, either the classical ipso substitution or copper catalysed iododeborylation pathway overall dominates the present iodination reaction. The features such as mild reaction conditions, operational simplicity, high to excellent yields, excellent functional group compatibility and low catalyst loading make this method potentially useful in organic synthesis.
- Tale,Toradmal,Gopula
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p. 84910 - 84919
(2015/10/28)
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- Rapid and efficient copper-catalyzed finkelstein reaction of (hetero)aromatics under continuous-flow conditions
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A general, rapid, and efficient method for the copper-catalyzed Finkelstein reaction of (hetero)aromatics has been developed using continuous flow to generate a variety of aryl iodides. The described method can tolerate a broad spectrum of functional groups, including N-H and O-H groups. Additionally, in lieu of isolation, the aryl iodide solutions were used in two distinct multistep continuous-flow processes (amidation and Mg-I exchange/nucleophilic addition) to demonstrate the flexibility of this method.
- Chen, Mao,Ichikawa, Saki,Buchwald, Stephen L.
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supporting information
p. 263 - 266
(2015/02/05)
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- One-pot transformation of carboxylic acids into nitriles
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A variety of aromatic and aliphatic carboxylic acids were smoothly converted into the corresponding nitriles in good yields in a one-pot procedure by treatment with ethyl iodide/K2CO3/18-crown-6, followed by sodium diisobutyl-tert-butoxyaluminium hydride (SDBBA-H), and finally treatment with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH), and aqueous ammonia. This method is useful for the conversion of various aromatic and aliphatic carboxylic acids into the corresponding nitriles in a one-pot procedure. A variety of aromatic and aliphatic carboxylic acids were smoothly converted into the corresponding nitriles in good yields in a one-pot procedure by treatment with ethyl iodide/K2CO3/18-crown-6, followed by sodium diisobutyl-tert-butoxyaluminium hydride (SDBBA-H), and finally treatment with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH), and aqueous ammonia. Copyright
- Miyagi, Kotaro,Moriyama, Katsuhiko,Togo, Hideo
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p. 5886 - 5892
(2013/09/23)
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- Facile preparation of aromatic esters from aromatic bromides with ethyl formate or DMF and molecular iodine via aryllithium
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Various aromatic bromides were treated with n-BuLi and subsequently with ethyl formate, followed by the reaction with ethanol and molecular iodine in the presence of K2CO3 to provide the corresponding aromatic ethyl esters in good yields. Moreover, aromatic bromides could be transformed into the corresponding aromatic methyl esters in good yields by the treatment with n-BuLi and subsequently with DMF, followed by the reaction with methanol, molecular iodine, and K2CO3. Some aromatics could be also converted into the corresponding aromatic esters in good yields by the treatment with n-BuLi, and subsequently with ethyl formate or DMF, followed by the reaction with molecular iodine and K2CO3. The present reactions offer a novel route for the transition-metal-free, carbon-monoxide-free, and therefore environmentally benign one-pot conversion of aromatic bromides and aromatics into aromatic esters.
- Ushijima, Sousuke,Moriyama, Katsuhiko,Togo, Hideo
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experimental part
p. 4701 - 4709
(2012/07/28)
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- Nickel-catalysed aromatic Finkelstein reaction of aryl and heteroaryl bromides
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A fast and efficient nickel-catalysed iodination reaction of aryl and heteroaryl bromides has been developed. The transformation was found to be general for a wide range of substrates and was used for the synthesis of iodo-PK11195, an imaging agent of Alzheimer's disease and iniparib, a compound used in the treatment of breast cancer.
- Cant, Alastair A.,Bhalla, Rajiv,Pimlott, Sally L.,Sutherland, Andrew
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supporting information; experimental part
p. 3993 - 3995
(2012/06/05)
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- Highly stereoselective 7-endo-trig /ring contraction cascade to construct pyrrolo[1,2- a ]quinoline derivatives
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With the cooperation of Cram's phenonium ion, a novel cascade reaction was illustrated to construct pyrrolo[1,2-a]quinolines as a sole diastereoisomer in good to excellent yields. Preliminary mechanistic studies revealed that the γ-lactam ring and electron-rich arene are important driving forces for ring contraction.
- Li, Xinyu,Li, Cheng,Zhang, Wenjing,Lu, Xiang,Han, Shiqing,Hong, Ran
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supporting information; experimental part
p. 1696 - 1699
(2010/09/05)
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- Synthesis of organometallic poly(dendrimer)s by macromonomer polymerization: effect of dendrimer size and structural rigidity on the polymerization efficiency
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Two series of first to third generation (G1-G3) oligoether dendrimers, one hearing a shorter spacer chain (C-O) and the other having a longer spacer branch (C-C-C-O) were prepared. Both series of compounds, containing two reactive C≡CH moieties on the dendrimer surface, were used as macromonomers and copolymerized with trans-[Pt(PEt3)2Cl2] to form organometallic poly(dendrimer)s by an outer-sphere-outer-sphere connection strategy. It was found that concentration of monomer used in the polymerization, the dendrimer generation, and, most strikingly, the length of the spacer were key factors that determined the polymerization efficiency. Hence, the structurally more rigid and compact C-O linked dendrimers formed poly(dendrimer)s with a higher degree of polymerization than the structurally less rigid and more bulky C-C-C-O dendrimers. This result was due to the higher tendency to form cyclic oligomers in the latter series of compounds. In addition, the differences in the polymerization efficiency among the three generations of dendrimers could be explained by the gradual decrease of reactive functional group density on the dendrimer surface.
- Cheung, Siu-Yin,Chow, Hak-Fun,Ngai, To,Wei, Xiaoling
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supporting information; experimental part
p. 2278 - 2288
(2009/10/23)
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- Sonogashira coupling applied in the synthesis of 1,2,4-oxadiazole-based nonsymmetrical liquid crystals
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A series of highly π-conjugated nonsymmetrical liquid crystals, based on the core 3,5-(disubstituted)-1,2,4-oxadiazole with a shape similar to a hockey stick, were successfully synthesized by convergent Sonogashira coupling reaction between the building blocks of aryl iodides and the corresponding terminal arylacetylenes, using 3-[4-(decyloxy)phenyl]-5-(haloaryl)-1,2,4-oxadiazoles or decyl 4-iodobenzoate (10) and terminal arylacetylenes. This versatile synthetic route yielded luminescent mesogens with smectic and nematic phases, typical of calamitic compounds. Georg Thieme Verlag Stuttgart.
- Gallardo, Hugo,Cristiano, Rodrigo,Vieira, Andre A.,Neves Filho, Ricardo A. W.,Srivastava, Rajendra M.
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p. 605 - 609
(2008/12/21)
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- The synthesis and fungicidal activities of 2,6-bis[(3-aryl)-s-triazolo[3,4- b]-[1,3,4]thiadiazole-6-yl]pyridines
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In search of better bioactive compounds, a series of novel 2,6-bis[(3-aryl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]pyridines 2 were synthesized in high yields by the cyclization of 3-aryl-4-amino-5-mercapto-1, 2, 4-triazoles 1 with 2,6-pyridine dicarboxylic acid. 2 exhibited good fungicidal activities against Cerospora beticola sacc. Copyright Taylor & Francis Group, LLC.
- Li, Dejiang,Long, Deqing,Fu, Heqing
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p. 2079 - 2087
(2007/10/03)
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- 2,2′-bipyridine: An efficient ligand in the cobalt-catalyzed synthesis of organozinc reagents from aryl chlorides and sulfonates
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The synthesis of functionalized arylzinc reagents from aromatic chlorides, triflates, or mesylates, via cobalt catalysis, is reported using 2,2′-bipyridine as a ligand in a mixture of acetonitrile and pyridine. This procedure allows the synthesis of a variety of functionalized arylzinc species in good to excellent yields. Some of these arylzinc compounds have been coupled with aromatic bromides under palladium catalysis. Georg Thieme Verlag Stuttgart.
- Kazmierski, Igor,Gosmini, Corinne,Paris, Jean-Marc,Périchon, Jacques
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p. 881 - 884
(2007/10/03)
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- Synthesis of C2-C3′N-linked macrocyclic taxoids. Novel docetaxel analogues with high tubulin activity
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Novel C2-C3′N-linked macrocyclic taxoids 4 bearing an aromatic ring at position C2 were synthesized. These compounds, tethered between N3′ and the C2-aromatic ring at the ortho, meta, or para position, were constructed by ring-closing metathesis. The para
- Querolle, Olivier,Dubois, Jo?lle,Thoret, Sylviane,Roussi, Fanny,Guéritte, Fran?oise,Guénard, Daniel
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p. 5937 - 5944
(2007/10/03)
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- Combination therapy
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The present invention relates to methods of treating cancer using a combination of at least two Akt inhibitors or a compound which is an inhibitor of Akt and an inhibitor of a protein kinase, which methods comprise administering to a mammal, either sequentially in any order or simultaneously, amounts of at least two therapeutic agents selected from a group consisting of a compound(s) which are inhibitors of Akt and compound(s) which are inhibitors of protein kinases. The invention also relates to methods of preparing such compositions.
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- Disubstituted acetylenes bearing heterobicyclic groups and heteroaromatic or phenyl groups having retinoid like activity
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Compounds of the formula where R1and R2, independently are alkyl groups having 2 to 8 carbons; R3is hydrogen or lower alkyl; X is S, O or N—R4where R4is hydrogen or lower alkyl; Y is phenyl or pyridyl
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Page column 18
(2010/01/30)
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- Palladium-catalyzed synthesis of biaryls from arylzinc compounds using N-chlorosuccinimide or oxygen as an oxidant
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In the presence of a catalytic amount of Pd2+ or Pd0, oxidative homo-coupling of arylzinc compounds was achieved by the use of N-chlorosuccinimide (NCS) or O2 as an oxidant. Different reaction pathways were involved in the catalytic reactions depending on the oxidants; NCS or O2 probably oxidized I- or Pd0 to I+ or Pd2+, respectively. This reaction disclosed a new and facile synthetic method of biaryls from aryl halides or arenes via arylzinc intermediates.
- Hossain, Kabir M.,Kameyama, Toru,Shibata, Takanori,Takagi, Kentaro
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p. 2415 - 2420
(2007/10/03)
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- Application of a new kinetic method in the investigation of cleavage reactions of haloaromatic radical anions
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A simple kinetic method based on competition kinetics is presented for the measurement of cleavage rate constants of radical anions over the range of 107 - 5 × 109 s-1 in aprotic solvents. The standard potential for the formation of the radical anions may be extracted from the kinetic analysis as well. The method employs electrochemical steady-state or optical detection techniques and is an extension of the redox catalysis approach described previously in the literature. The applicability of the method is illustrated through a systematic study of the cleavage reactions for a number of short-lived haloaromatic radical anions. Interestingly, the radical anion of iodobenzene is found to be an intermediate in the homogeneous reduction of iodobenzene, even though recent investigations have shown that the corresponding heterogeneous reduction at an electrode surface proceeds by a concerted electron transfer-bond cleavage process. The nature of the cleavage reactions is discussed in terms of the activation driving force plot of the cleavage rate constants versus the relevant Gibbs energies. While the exergonic cleavage reactions follow a simple decay mechanism taking place at the halogen site, the endergonic processes are best described as intra-molecular electron transfers from the substituent to the carbon-halogen bond. Nevertheless, the overall intrinsic barrier is found to be relatively small (27-39 kJ mol-1) and it is suggested that the endergonic reactions may proceed by a stepwise mechanism, in which a σ* radical anion is formed as an intermediate prior to the formation of the dissociated products, the aryl radical and the halide. The above conclusions were supported by semi-empirical PM3 calculations of structures and charge distributions in the radical anions.
- Enemaerke, Rasmus J.,Christensen, Torben B.,Jensen, Henrik,Daasbjerg, Kim
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p. 1620 - 1630
(2007/10/03)
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- 3-D QSAR analysis of inhibition of murine soluble epoxide hydrolase (MsEH) by benzoylureas, arylureas, and their analogues
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Two hundred and seventy-one compounds including benzoylureas, arylureas and related compounds were assayed using recombinant murine soluble epoxide hydrolase (MsEH) produced from a baculovirus expression system. Among all the insect growth regulators assayed, 18 benzoylphenylurea congeners showed weak activity against MsEH. Newly synthesized cyclohexylphenylurea, 1-benzyl-3-phenylurea, and 1,3-dibenzylurea analogues were rather potent. The introduction of a methyl group at the para-position of the phenyl ring of cyclohexylphenylurea enhanced the activity 6-fold, though similar substituent effects were not seen for any of the benzoylphenylureas. The activities of these compounds, including several previously reported compounds, such as dicyclohexylurea, diphenylurea, and their related analogues (Morisseau et al., Proc. Natl. Acad. Sci., 1999, 96, 8849), were quantitatively analyzed using comparative molecular field analysis (CoMFA), a three-dimensional quantitative structure-activity relationship (3-D QSAR) method. Both steric and electrostatic factors contributing to variations in the activity were visualized using CoMFA. CoMFA results showed that one side of the cyclohexylurea moiety having a trans-amide conformation (A-ring moiety) is surrounded by large sterically unfavorable fields, while the other side of A-ring moiety and the other cyclohexyl group (B-ring moiety) is encompassed by sterically favored fields. Electrostatically negative fields were scattered around the entire molecule, and a positive field surrounds the carbon of the carbonyl group. Hydrophobic fields were visualized using Kellogg's hydropathic interaction (HINT) in conjunction with CoMFA. Hydrophobically favorable fields appeared beside the 4- and 4'-carbon atoms of the cyclohexyl groups, and hydrophobically unfavorable fields surrounded the urea bridge. The addition of the molecular hydrophobicity, it> /it>, to CoMFA did not improve the correlation significantly. The ligand-binding interactions shown by X-ray crystallographic data were rationalized using the results of the CoMFA and HINT analyses, and the essential physicochemical parameters for the design of new MsEH inhibitors were disclosed. Copyright (C) 2000 Elsevier Science Ltd.
- Nakagawa, Yoshiaki,Wheelock, Craig E.,Morisseau, Christophe,Goodrow, Marvin H.,Hammock, Bruce G.,Hammock, Bruce D.
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p. 2663 - 2673
(2007/10/03)
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- Method for inhibiting gene expression promoted by AP1 protein with RAR beta selective retinoids and method for treatment of diseases and conditions with such retinoids
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Retinoid compounds which repress expression of the gene promoted by AP1 protein but which do not significantly activate expression of the genes having RA-responsive elements in their promoter region through RAR alpha and RAR GAMMA receptor subtypes, are u
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- Trisubstituted phenyl derivatives having retinoid agonist, antagonist or inverse agonist type biological activity
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Compounds of the formula where the symbols have the meaning defined in the specification, have retinoid, retinois antagonist or retinoid inverse agonist type biological activity.
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- Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities
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Aryl-substituted and aryl and (3-oxo-1-propenly)-substituted benzopyran, benzothiopyran, 1,2-dihydroquinoline, and 5,6-dihydronaphthalene derivatives have retinoid negative hormone and/or antagonist-like biological activities. The invented RAR antagonists can be administered to mammals, including humans, for the purpose of preventing or diminishing action of RAR agonists on the bound receptor sites. Specifically, the RAR agonists are administered or coadministered with retinoid drugs to prevent or ameliorate toxicity or side effects caused by retinoids or vitamin A or vitamin A precursors. The retinoid negative hormones can be used to potentiate the activities of other retinoids and nuclear receptor agonists. For example, the retinoid negative hormone called AGN 193109 effectively increased the effectiveness of other retinoids and steroid hormones in in vitro transactivation assays. Additionally, transactivation assays can be used to identify compounds having negative hormone activity. These assays are based on the ability of negative hormones to down-regulate the activity of chimeric retinoid receptors engineered to possess a constitutive transcription activator domain.
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- SYNTHESIS AND USE OF RETINOID COMPOUNDS HAVING NEGATIVE HORMONE AND/OR ANTAGONIST ACTIVITIES
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2,2-Dialkyl-4-aryl-substituted benzopyran and benzothiopyran derivatives of the formula STR1 where the symbols have the meaning described in the specification, have retinoid negative hormone and/or antagonist-like biological activities. The invented RAR antagonists can be administered to mammals, including humans, for the purpose of preventing or diminishing action of RAR agonists on the bound receptor sites. Specifically, the RAR agonists are administered or coadministered with retinoid drugs to prevent or ameliorate toxicity or side effects caused by retinoids or vitamin A or vitamin A precursors. The retinoid negative hormones can be used to potentiate the activities of other retinoids and nuclear receptor agonists.
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- Substituted diaryl or diheteroaryl methanes, ethers and amines having retinoid agonist, antagonist or inverse agonist type biological activity
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Compounds of the formula where the symbols have the meaning defined in the specification, have retinoid, retinoid antagonist or retinoid inverse agonist type biological activity.
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- Nitrogen dioxide - Sodium iodide as an efficient reagent for the one- pot conversion of aryl amines to aryl iodides under nonaqueous conditions
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Successive treatment of aromatic amines with liquid nitrogen dioxide and powdered sodium iodide in acetonitrile at -20 °C, followed by usual work- up, gave the corresponding aryl iodides in good yield. This method worked especially well for less basic amines bearing electron-withdrawing substituents.
- Suzuki, Hitomi,Nonoyama, Nobuaki
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p. 4533 - 4536
(2007/10/03)
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- Acetylenes disubstituted with a phenyl or heteroaryl group and a 2-thio-1,2,3,4-tetrahdroquinolinyl, 2-alkylthio-3,4-dihydroquinolinyl or 2-alkoxy-3,4-dihydroquinolinyl group having retinoid-like biological activity
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Compounds of the formula STR1 where the symbols are defined as in the specification.
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- [(3""-thioxacyclohex-1""-enyl)]-but-3'-ene-1'-ynyl]aryl and [(3""-thioxacyclohex-1""-enyl)]-but-3'-ene-1'-ynyl]heteroaryl carboxylic acids and esters having retinoid-like biological activity
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Compounds of the formula STR1 where R 1, R 2, R 3, and R 4 independently are H or lower alkyl of 1 to 10 carbons; R 5 is lower alkyl of 1 to 10 carbons, fluoro, chloro, bromo, iodo, nitro, or fluoroalkyl having 1 to 10 carbons; m is an integer having the
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- Acetylenes disubstituted with a 5-amino or substituted 5-amino substituted tetrahydronaphthyl group and with an aryl or heteroaryl group having retinoid-like biological activity
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Compounds of the formula STR1 having retinoid like biological activity.
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