- Next Generation of Guanidine Quinoline Copper Complexes for Highly Controlled ATRP: Influence of Backbone Substitution on Redox Chemistry and Solubility
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Ligands DMEG6etqu, TMG6etqu, DMEG6buqu, and TMG6buqu were developed on the basis of guanidine quinoline (GUAqu) ligands 1,3-dimethyl-N-(quinolin-8-yl)imidazolidin-2-imine (DMEGqu) and 1,1,3,3-tetramethyl-2-(quinolin-8-yl)guanidine (TMGqu). These ligands feature an alkyl substituent at the C6 of the quinoline backbone. The synthetic strategy developed here enables inexpensive syntheses of any kind of C6-substituted GUAqu ligands. On one hand, the alkylation increases the solubility of corresponding copper complexes in apolar atom transfer radical polymerization (ATRP) monomers like styrene. On the other hand, it has a significant electronic influence and thus an effect on the donor properties of the new ligands. Seven CuI and CuII complexes of DMEG6etqu and TMG6etqu have been crystallized and were studied with regard to their structural and electrochemical properties. CuI and CuII complexes of DMEG6buqu and TMG6buqu turned out to be perfectly soluble in pure styrene even at room temperature, which makes them excellent catalysts in the ATRP of apolar monomers. The key characteristics of the ATRP equilibrium, KATRP and kact, were determined for the new complexes. In addition, we used our recently developed DFT methodology, NBO analysis, and isodesmic reactions to predict the influence of the introduced alkyl substituents. It turned out that high conformational freedom in the complex structures leads to a significant uncertainty in prediction of the thermodynamic properties.
- R?sener, Thomas,Hoffmann, Alexander,Herres-Pawlis, Sonja
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- A Systematic Study on the Synthesis of n-Butyl Substituted 8-Aminoquinolines
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(Chemical Equation Presented) A systematic study on the synthesis of 8-aminoquinoline derivatives with an n-butyl group at each alternate position of the quinoline ring was carried out. Skraup Reaction and its Doebner-von Miller variation were used to obtain most of the quinoline ring except for the 2-butyl-8-aminoquinolines and 4-butyl-8-aminoquinolines where the commercially available methylquinoline derivatives were used as precursors. The structures of the synthesized compounds were characterized by FTIR, 1H-NMR, COSY, 13C-NMR and HRMS spectra.
- Koseoglu, Ahmet,Gul, Turan,Acar, Ali Ersin
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p. 263 - 270
(2016/02/10)
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- 5-n-butyl-1H-benzotriazole synthesis process
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The present invention discloses a 5-n-butyl-1H-benzotriazole synthesis process, which comprises: adding concentrated sulfuric acid to acetic anhydride in a dropwise manner, and adding 4-n-butyl aniline in a dropwise manner to prepare 4-n-butyl acetanilide; adding a mixed acid solution comprising 65% concentrated nitric acid and acetic anhydride to the 4-n-butyl acetanilide in a dropwise manner to synthesize 4-n-butyl-2-nitro acetanilide; synthesizing 4-n-butyl-2-nitroaniline by using the 4-n-butyl-2-nitro acetanilide, 95% ethanol and 40% sodium hydroxide as raw materials; under the effect of a catalyst, using the 4-n-butyl-2-nitroaniline and dehydrated alcohol and sequentially using nitrogen and hydrogen to convert under a closed condition to prepare 4-n-butyl-o-phenylenediamine; and adding the 4-n-butyl-o-phenylenediamine, water and sodium nitrite to an autoclave to synthesize the 5-n-butyl-1H-benzotriazole. According to the present invention, the process equipment is simple, and the product yield is high.
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Paragraph 0011
(2016/12/01)
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- MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS
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The compounds represented by Formula (I) or pharmaceutically acceptable salts thereof: with U, W, X, Y, Z, p and ring A as defined in claim 1. Those compounds are useful for the treatment or prevention of bacteria infections. The variables of Formula (I) are as described herein. Pharmaceutically acceptable compositions comprise the compounds of Formula (I) or pharmaceutically acceptable salts thereof and pharmaceutically acceptable carriers, adjuvants, or vehicles. Methods of treating bacteria infections employ such compounds or pharmaceutically acceptable salts thereof.
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Paragraph 000176
(2016/12/26)
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- BENZIIMIDAZOLE AND IMIDAZOPYRIDINE DERIVATIVES AS SODIUM CHANNEL MODULATORS
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The invention relates to benzimidazole and imidazopyridine derivatives, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes. More particularly the invention relates to new Nav1.8 modulators of formula (I) or pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7. X and Y are as defined in the description. Nav1.8 modulators are potentially useful in the treatment of a wide range of disorders, particularly pain.
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Page/Page column 82; 83; 84
(2013/08/15)
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- Photochemistry of (2-nitrophenyl)diazomethane studied by the matrix isolation technique. (Nitrophenyl)carbene to (carboxylphenyl)nitrene rearrangement by successive reduction of the nitro group with the carbenic center
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Irradiation (λ > 350 nm) of (2-nitrophenyl)diazomethane (1) matrix-isolated in Ar at 10 K provided 2-nitrosobenzaldehyde (3) presumably as a result of intramolecular oxygen migration in (2-nitrophenyl)carbene (2). Upon further irradiation (λ > 350 nm), 3 was decomposed to give a mixture of 2,1-benzisoxazol-3(1H)-one (4) and carbonylcyclopentadiene imine (5) along with CO2. The oxazolone (4) underwent decarboxylation to give 5 upon irradiation with shorter wavelength light (λ > 300 nm) but not at longer wavelength (λ > 350 nm), suggesting 4 is not the direct precursor for 5 in the photolysis of 3. Irradiation (λ > 350 nm) of (4-n-butyl-2-nitrophenyl)diazomethane (1b) under similar conditions resulted in the formation of carbonyloximinocyclohexadienylidene (7) which then produced the oxazolone (4b) and the imine (5b) upon further irradiation, suggesting that a 1,4-biradical generated as a result of abstraction of H at the ortho position by the photoexcited nitroso group was involved in the reaction of 3 forming 4. (2-Carboxyphenyl)nitrene (9) generated by 1,4-OH shift in the 1,4-biradical was postulated as an intermediate leading to 5, and this was actually demonstrated by independent generation of 9 by the photolysis of 2-azidobenzoic acid (8).
- Tomioka, Hideo,Ichikawa, Naoki,Komatsu, Kazunori
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p. 8045 - 8053
(2007/10/02)
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- Nouveaux diamino-3,4 phenylalcanes et leur transformation en benzimidazolemethanethiols-2
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We report five o-phenylenediamines which are substituted by an aliphatic chain containing n carbon atoms (n = 4, 6, 8, 10, 12).We describe a well adapted general synthetic method using Schmidt's reaction.The diamines were then transformed into 2-benzimidazolemethanethiols and their related S-methyl derivatives which structures were checked by (1)H NMR.
- Krati, Noureddine,Roizard, Denis,Brembilla, Alain,Lochon, Pierre
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p. 443 - 448
(2007/10/02)
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