- (Trifluoromethylselenyl)methylchalcogenyl as Emerging Fluorinated Groups: Synthesis under Photoredox Catalysis and Determination of the Lipophilicity
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The synthesis of molecules bearing (trifluoromethylselenyl)methylchalcogenyl groups is described via an efficient two-step strategy based on a metal-free photoredox catalyzed decarboxylative trifluoromethylselenolation with good yields up to 88 %, which raised to 98 % in flow chemistry conditions. The flow methods allowed also to scale up the reaction. The mechanism of this key reaction was studied. The physicochemical characterization of these emerging groups was performed by determining their Hansch–Leo lipophilicity parameters with high values up to 2.24. This reaction was also extended to perfluoroalkylselenolation with yields up to 95 %. Finally, this method was successfully applied to the functionalization of relevant bioactive molecules such as tocopherol or estrone derivatives.
- Grollier, Kevin,De Zordo-Banliat, Arnaud,Bourdreux, Flavien,Pegot, Bruce,Dagousset, Guillaume,Magnier, Emmanuel,Billard, Thierry
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supporting information
p. 6028 - 6033
(2021/03/15)
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- Impregnated copper ferrite on mesoporous graphitic carbon nitride: An efficient and reusable catalyst for promoting ligand-free click synthesis of diverse 1,2,3-triazoles and tetrazoles
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Magnetic CuFe2O4/g-C3N4 hybrids were synthesized through a facile method and their catalytic performances were evaluated in click chemistry for the first time. The structural and morphological characterization of prepared materials was carried out by different techniques such as X-ray diffraction, high-resolution transmission electron microscopy, field emission scanning electron microscopy, Fourier infrared spectroscopy, vibrating sample magnetometry, thermogravimetric analysis, and N2 adsorption–desorption analysis (Brunauer–Emmett–Teller surface area). The utilization of magnetic CuFe2O4/g-C3N4 enabled superior performance in the one-pot azide–alkyne cycloaddition reaction in water using alkyl halides and epoxides as azide precursors without the need of any additional agents. The present system is broad in scope and especially practical for the synthesis of macrocyclic triazoles and also tetrazoles. In addition, the catalytic system highly fulfills the demands of “green click chemistry” with its convenient conditions, especially easy access to a variety of significant products in low catalyst loading and simple work-up and isolation procedure.
- Khalili, Dariush,Rezaee, Meysam
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- Triazole-amide isosteric pyridine-based supramolecular gelators in metal ion and biothiol sensing with excellent performance in adsorption of heavy metal ions and picric acid from water
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Pyridine-based small molecular gelators 1-4, having a triazole-amide isosteric relationship, have been synthesized. Compounds 1-3 exhibit excellent gelation from DMSO-H2O (1?:?2, v/v), while compound 4 forms a gel in the presence of Ag+ ions in DMSO-H2O (1?:?2, v/v). The change from triazole to isosteric amide has a marked effect on the gelling abilities, minimum gelation concentrations (mgc), thermal stability, mechanical properties, metal ion-responsive character and adsorption properties of the structures, as established by various techniques. All the gels have been successfully applied in sophisticated sensing kits for the selective detection of Cu2+ and Ag+ ions and thiol-containing amino acids. The triazole-based gelators 1 and 3 adsorb heavy metal ions from water with greater efficiency than the isosteric amide-based gelators. The metallogel 4-Ag+ can be used in the efficient removal of picric acid (a nitro explosive) from water.
- Panja, Atanu,Ghosh, Kumaresh
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p. 934 - 945
(2019/01/09)
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- Synthesis of new lariat ethers containing polycyclic phenols and heterocyclic aromatic compound on graphite surface via mannich reaction
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Synthesis of novel lariat ethers containing polycyclic phenols and heterocyclic aromatic compound using graphite via Mannich reaction are herein described. For this purpose N-(methoxymethyl) azacrown ether 4 was synthesized in nearly quantitative yield. The reaction of N-(methoxymethyl) azacrown ether 4 with polycyclic phenols and heterocyclic aromatic compound was performed in 10-20 min in the presence of graphite. The graphite powder can be reused up to five times after simple washing with acetone.
- Sharghi,Khalifeh,Salimi Beni
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experimental part
p. 275 - 288
(2010/11/05)
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- Fibrinogen receptor antagonists and their use
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This invention relates to novel fused bicyclic compounds of the general formula (I): wherein the symbols are defined herein, to pharmaceutical compositions containing the compounds, processes for preparing the compounds, and to methods of using the compounds, alone or in combination with other therapeutic agents. The compounds are antagonists of the platelet glycoprotein IIb/IIIa fibrinogen receptor complex, and are therefore useful for the inhibition of platelet aggregation, and for the treatment of thrombotic diseases and other diseases.
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Page/Page column 58
(2010/08/04)
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- Guanidino substituted isoindolones as novel glycoprotein IIb-IIIa receptor antagonists
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Design and synthesis of a novel potent glycoprotein IIb-IIIa (GP IIb-IIIa) receptor antagonist based on isoindolone skeleton has been described. This scaffold has been derived from earlier reported pseudopeptides. Synthesis by a novel route has been achieved. Few molecules show very potent in vitro activity. Further identification of probable additional hydrogen bond donor site has been described.
- Lal, Bansi,Gangopadhyay, Ashok K.,Jagtap,Tanpure, Rajendra,Rao,Gupte, Ravindra D.,Subbarayan,Asudani, Gope
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p. 1815 - 1832
(2008/09/18)
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- Reduction of an amido zinc(II) phthalocyanine by diborane
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1,2-Dicyano-4,5-di[(N,N-dimethylaminocarbonyl)methoxy]benzene (5) was synthesized in 80% yield from the corresponding 1,2-dibromo derivative 4. Octa(peripheral-amide)substituted zinc(II) phthalocyanine 6 was obtained from 5 and zinc acetate in the presenc
- Strassert, Cristian A.,Dicelio, Lelia E.,Awruch, Josefina
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p. 799 - 802
(2007/10/03)
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- Synthesis, characterization and ion transportation studies of some novel cyclophane amides
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Various novel cyclophane amides with a large cavity have been synthesized. The structures of cyclophane amides 14 and 15 were resolved using XRD studies. Cyclophane amide 28 shows a shift in λmax in the UV/Vis. spectra when treated with Cu (II) ion as well as with Pb (II) ion. Ion transportation studies were carried out with cyclophane amide 14 which proved that the Na+ ion passes through the cavity while K+ ions are retained.
- Rajakumar, Perumal,Rasheed, A. Mohammed Abdul
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p. 5351 - 5362
(2007/10/03)
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- FIBRINOGEN RECEPTOR ANTAGONISTS AND THEIR USE
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This invention relates to novel fused bicyclic compounds of the general formula (I): wherein the symbols are defined herein, to pharmaceutical compositions containing the compounds, processes for preparing the compounds, and to methods of using the compounds, alone or in combination with other therapeutic agents. The compounds are antagonists of the platelet glycoprotein IIb/IIIa fibrinogen receptor complex, and are therefore useful for the inhibition of platelet aggregation, and for the treatment of thrombotic diseases and other diseases.
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Page/Page column 72
(2010/02/11)
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- A molecular loop with interstitial channels in a chiral environment: Exploration of the chemistry of Mo24+ species with chiral and non-chiral dicarboxylate anions
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An enantiomerically pure chiral loop containing two cis-Mo2(DAniF)22+ (DAniF = di-p-anisylformamidinate) units was obtained by reaction of cis-[Mo2(DAniF)2(NCMe)4] (BF4)2 with a chiral dicarboxylate which is easily prepared from hydroquinone and ethyl (S)-lactate. The compound crystallizes in the non-centrosymmetric I222 space group with molecules stacking so as to form channels capable of hosting guest molecules such as CH2Cl2. These properties of the compound, which has been synthesized in high yield, makes it promising for applications in stereoselective catalysis. Similar reactions with isomeric dicarboxylate linkers, as well as with some non-chiral ligands, were studied. The nature of the products depends on the bite angle of the ligand.
- Berry, John F.,Cotton, F. Albert,Ibragimov, Sergey A.,Murillo, Carlos A.,Wang, Xiaoping
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p. 4297 - 4302
(2007/10/03)
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- Synthetic Ionophores. Part 8. Amide-Ether-Amine-Containing Macrocycles: Synthesis, Transport and Binding of Metal Cations
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1,2-Bis(ethoxycarbonylmethoxy)benzene undergoes 1:1 stoichiometric condensation with 1,2-diaminoethane, 1,3-diaminopropane, diethylenetriamine and 3,3'-diaminodipropylamine to form the macrocycles 2a, 2b, 3a and 4a respectively.Methyl iodide, ethyl bromoa
- Kumar, Subodh,Singh, Rajinder,Singh, Harjit
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p. 3049 - 3054
(2007/10/02)
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- Anticoccidial activity of crown polyethers
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Anticoccidial activity in vitro against Eimeria tenella is reported for crown polyethers with ring sizes from 14 to 30 atoms. The most potent compounds, 4 and 9, were found active at 0.33 ppm, but none were active in vivo. Test results are discussed in te
- Brown,Foubister
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p. 590 - 592
(2007/10/02)
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- Synthesis and Characterization of Some Bifunctional 2B:2:1 Cryptands
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Methods for the synthesis of aromatic substituted diaza-polyoxamacrobicyclic compounds (benzocryptands) are described.New synthetic routes to cryptand precursors are developed and improvements in cryptand synthesis discussed and employed to prepare some bifunctional cryptands.
- Gansow, Otto A.,Kausar, A. Rashid,Triplett, Kelly B.
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p. 297 - 302
(2007/10/02)
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- Synthesis of 7,8,9,10,11,12,20,21,22,23,24,25-Dodecahydrodibenzotetraoxacyclodocosin, a Crown Ether
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A number of symmetrical diesters and an unsymmetrical type have been synthesised from pyrocatechol.Under conditions in which intramolecular acyloin formation was anticipated the product from one symmetrical compound, ethyl 4-(o-ethoxycarbonylpropoxyphenoxy)butyrate, was a cyclic bis-β-keto-ester resulting in reasonable yield from intermolecular Dieckmann cyclisation.Hydrolysis to the 9,22 diketone, and its reduction to 7,8,9,10,11,12,20,21,22,23,24,25-dodecahydrodibenzotetraoxacyclodocosin 'dibenzo-22-crown-4', proceeded smoothly.An unsymmetrical intermediate, methyl 4-(o-ethoxycarbonylmethoxypropylphenoxy)butyrate, was prepared for similar cyclisation and in preliminary experiments appeared to give acyloin and β-keto-ester products.The method represents a different approach to crown ether systems of certain types.
- Tyman, John H. P.,Grundy, Jesse,Brown, George R.
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p. 336 - 343
(2007/10/02)
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