- One-pot synthesis of 4-aryl-2-aminothiazoles from styrenes and thioureas promoted by tribromoisocyanuric acid
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A simple and efficient one-pot protocol has been developed for the conversion of styrenes into 4-aryl-2-aminothiazoles using readily available starting materials. Tribromoisocyanuric acid was successfully used for the co-bromination and oxidation of styrenes to give phenacyl bromides, which in the presence of thioureas produced the corresponding 4-aryl-2-aminothiazoles in 48–70% yield. The protocol involves three reactions in one process: a tandem (formation of phenacyl bromides from styrenes) followed by a telescoped (conversion to thiazole) reaction.
- de Andrade, Vitor S.C.,de Mattos, Marcio C.S.
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supporting information
(2020/07/03)
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- Selective Asymmetric Transfer Hydrogenation of α-Substituted Acetophenones with Bifunctional Oxo-Tethered Ruthenium(II) Catalysts
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A practical method for the asymmetric transfer hydrogenation of α-substituted ketones was developed utilizing oxo-tethered N-sulfonyldiamine-ruthenium complexes. Reduction by HCO2H and HCO2K in a mixed solvent of EtOAc/H2O allowed for the selective synthesis of halohydrins from 2-bromoacetophenone (98%) and 2-chloroacetophenone (>99%), leading to suppressed undesired side reactions stemming from formylation under the typical reaction conditions using an azeotropic 5:2 mixture of HCO2H and Et3N. A range of functional groups, such as halogens, methoxy, nitro, dimethylamino, and ester groups, were well tolerated, highlighting the potential of this method. Nearly complete selectivity with a preferable ee was maintained even with a substrate/catalyst (S/C) ratio of 5000. This catalyst system was also effective for the asymmetric reduction of α-sulfonated ketones without eroding the leaving group. (Figure presented.).
- Yuki, Yamato,Touge, Taichiro,Nara, Hideki,Matsumura, Kazuhiko,Fujiwhara, Mitsuhiko,Kayaki, Yoshihito,Ikariya, Takao
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supporting information
p. 568 - 574
(2017/12/13)
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- One-pot synthesis of α-bromo- and α-azidoketones from olefins by catalytic oxidation with in situ-generated modified IBX as the key reaction
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Simple one-pot protocols for the syntheses of α-bromoketones and α-azidoketones starting from olefins have been developed by employing catalytic oxidation of the intermediary bromohydrins with in situ-generated modified IBX as the key reaction. The improved procedure involves initial formation of bromohydrin by the reaction of olefin with NBS in acetonitrile-water mixture (1:1) at rt followed by oxidation with in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX), produced in catalytic amounts from 3,4,5,6-tetramethyl-2-iodobenzoic and Oxone. α-Bromoketones are further converted in the same pot to the corresponding α-azidoketones using NaN3/NaHCO3. The one-pot conversions are versatile for a variety of olefins that include cyclic as well as acyclic aliphatic olefins and electron-rich and electron-deficient styrenes. Chemoselective bromohydroxylation of electron-rich double bond and subsequent oxidation to the α-bromoketone is demonstrated for a substrate that contains both electron-rich and deficient double bonds.
- Chandra, Ajeet,Parida, Keshaba Nanda,Moorthy, Jarugu Narasimha
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p. 5827 - 5832
(2017/09/09)
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- Synthesis and characterization of novel oxime derivatives
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Background: The synthesis of effective drugs are very important for the scientist. The various biological effects of the thiazole, oxime and ether functional groups are well known properties by the drug developers. So we have synthesised new molecules which contains three of them on the same molecules. Methods: The acetophenone derivatives have been used for synthesis new oximes. The synthetic pathway includes mainly four steps. s1. α-Bromination of acetophenone derivatives, s2. Synthesis of thiazole ring using brominated acetophenones, s3. Synthesis of ethers using synthesised thiazole, s4. Synthesis of oximes. Results: The synthesised molecules characterised using IR,1H-NMR, 13C-NMR and elementel analysis methods. Conclusion: The new oximes which include thiazole and ether groups have been synthesised using acetophenone derivatives.
- Arslan, Taner,Keskin, Serhat,Demirayak, Seref
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p. 672 - 677
(2017/01/13)
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- Highly Efficient Synthesis of α-Halomethylketones via Ce(SO4)2/Acid Co-Catalyzed Hydration of Alkynes
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A general atom-economical approach for the synthesis of α-halomethyl ketones is demonstrated through Ce(SO4)2/acid co-catalyzed hydration of a wide range of haloalkynes. The reactions are conducted under convenient conditions and provide products with excellent regioselectivity in good to excellent yields, with broad substrate scope. This protocol is an alternative to conventional α-halogenation of ketones.
- Zou, Huaxu,Jiang, Jun,Yi, Niannian,Fu, Wenqiang,Deng, Wei,Xiang, Jiannan
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supporting information
p. 1251 - 1254
(2016/12/27)
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- An amide compound, wherein the intermediate and the process for the preparation of intermediate
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The invention discloses preparation methods of amide-type compound 1 and intermediate 8 and the intermediate 8. The preparation method of the compound 1 comprises: in the solvent with alkali, the compound 8 is hydrolyzed, and the compound 1 is obtained; w
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Paragraph 0109; 0118; 0119
(2016/10/10)
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- Method for preparing organic bromide by using micro-channel reactor
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The invention discloses a method for preparing an organic bromide by using a micro-channel reactor. The method comprises the step of: performing a bromination reaction on a homogeneous solution formed by a compound shown in a formula I and a solvent and a homogeneous solution formed by a bromination agent and a solvent in the micro-channel reactor to obtain the organic bromide represented by a formula II, wherein the bromination reaction time is 1-10 minutes; the bromination reaction temperature is DEG C to 60 DEG C. The preparation method disclosed by the invention is extremely short, accurate to control reaction condition, high in safety and suitable for quick preparation of products, can be used for continuously production, and is low in cost. Moreover, by using the micro-channel reactor to prepare the organic bromide, the selectivity of reaction raw materials is high and the purity of a targerted compound is good, so that the preparation method is suitable for industrial production on a large scale. R1-H-R1-BrI II.
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Paragraph 0071; 0072; 0073; 0074; 0075
(2016/11/28)
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- Synthesis of phenacyl bromides via K2S2O 8-mediated tandem hydroxybromination and oxidation of styrenes in water
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Non-transition metal-catalyzed synthesis of phenacyl bromides was achieved through K2S2O8-mediated tandem hydroxybromination and oxidation of styrenes. The advantages of this reaction are its excellent functional group compatibility, mild reaction conditions (60 °C) and use of pure water as reaction medium. Based upon experimental observations, a plausible reaction mechanism is proposed.
- Jiang, Qing,Sheng, Wenbing,Guo, Cancheng
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p. 2175 - 2179
(2013/09/24)
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- Direct and selective benzylic oxidation of alkylarenes via C-H abstraction using alkali metal bromides
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A direct benzylic oxidation of alkylarenes via C-H bond abstraction was developed using alkali metal bromides and oxidants under mild conditions. This reaction proceeded with excellent selectivity by thermal oxidation or photooxidation to provide a broad range of carbonyl compounds containing electron-deficient aryl carbonyl compounds in high yields.
- Moriyama, Katsuhiko,Takemura, Misato,Togo, Hideo
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supporting information; experimental part
p. 2414 - 2417
(2012/06/18)
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- SUBSTITUTED IMIDAZOLE DERIVATIVES FOR TREATMENT OF ALZHEIMERS DISEASE
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The present invention provides imidazole derivatives of Formula (I) and pharmaceutically acceptable salts thereof. These compounds are useful in the treatment of RAGE-mediated diseases such as Alzheimer's Disease. The present invention further relates to
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Page/Page column 22; 25
(2011/04/25)
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- CRYSTALLINE FORMS OF [3-(4- -PHENOXY)-PROPYL]-DIETHYL-AMINE
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The present invention relates to crystalline forms of [3-(4-{2-butyl-1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethylamine (“COMPOUND I”) useful in the treatment of RAGE mediated diseases.
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Page/Page column 6
(2008/12/04)
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- Process for the production of basic substituted alkyltheophylline derivatives
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There is described a process for the production of theophylline derivatives of the formula STR1 where T is the theophyllinyl-(7)-residue, Alk is a straight or branched alkylene chain having 2 to 4 carbon atoms, R is hydrogen or a methyl group, n is 1 or 2
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