- Synthesis method of 3-bromoquinoline compound
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The invention provides a synthesis method of a 3-bromoquinoline compound. The invention belongs to the field of medical chemical synthesis. The synthesis method comprises the following steps: taking 1, 1, 3, 3-tetramethoxypropane 2 as a raw material to react with bromine to obtain an intermediate 3, obtaining an intermediate 4 from the intermediate 3 under the action of alkali, and reacting the intermediate 4 with a substituted aniline compound to obtain the 3-bromoquinoline compound 1, wherein R1 and R2 are selected from any one of hydrogen, alkyl, alkoxy, halogen, ester, nitro, trifluoromethyl, trifluoromethoxy, dimethylamino, acetyl and methylthio. The synthesis method of the 3-bromoquinoline compound has the advantages of few reaction steps, simplicity in operation, cheap and easily available raw materials, high yield, easiness in purification and easiness in amplified production.
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Paragraph 0025; 0028-0031
(2019/07/04)
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- Visible-Light-Photosensitized Aryl and Alkyl Decarboxylative Functionalization Reactions
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Despite significant progress in aliphatic decarboxylation, an efficient and general protocol for radical aromatic decarboxylation has lagged far behind. Herein, we describe a general strategy for rapid access to both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters followed by their successive use in divergent carbon–heteroatom and carbon–carbon bond-forming reactions. Identification of a suitable activator for carboxylic acids is the key to bypass a competing single-electron-transfer mechanism and “switch on” an energy-transfer-mediated homolysis of unsymmetrical σ-bonds for a concerted fragmentation/decarboxylation process.
- Patra, Tuhin,Mukherjee, Satobhisha,Ma, Jiajia,Strieth-Kalthoff, Felix,Glorius, Frank
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supporting information
p. 10514 - 10520
(2019/07/12)
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- Visible-Light Photocatalyzed Deoxygenation of N-Heterocyclic N-Oxides
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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
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supporting information
p. 7712 - 7716
(2019/01/03)
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- Actinide-Based Porphyrinic MOF as a Dehydrogenation Catalyst
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Uranyl–organic frameworks (UOFs) have recently been the object of many research endeavors due to the unique coordination mode of uranyl ions and their attractive physicochemical properties. Here, a new (3,4)-connected UOF (U-IHEP-4) assembled from uranyl and porphyrin ligand tetrakis(4-carboxyphenyl)porphyrin (H4TCPP) is reported, which represents the first case of actinide porphyrinic MOFs. Adsorption experiments in DMF solution demonstrated that U-IHEP-4 selectively adsorbs positively charged dyes, which is in line with its negatively charged framework and large pore volume ratio (90 %). Remarkably, U-IHEP-4 exhibited high catalytic activity for the dehydrogenation of N-heterocycles to synthesize the corresponding aromatic heterocycles and it can be used as an efficient heterogeneous catalyst.
- Hu, Kong-Qiu,Huang, Zhi-Wei,Zhang, Zhi-Hui,Mei, Lei,Qian, Bing-Bing,Yu, Ji-Pan,Chai, Zhi-Fang,Shi, Wei-Qun
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supporting information
p. 16766 - 16769
(2018/10/31)
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- Copper-catalyzed oxygen atom transfer of N-oxides leading to a facile deoxygenation procedure applicable to both heterocyclic and amine N-oxides
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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
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supporting information
p. 7035 - 7038
(2015/04/22)
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- CONDENSED-CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DIODE INCLUDING THE CONDENSED-CYCLIC COMPOUND
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A condensed-cyclic compound and an organic light-emitting diode including the condensed-cyclic compound.
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Page/Page column
(2014/04/03)
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- Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ
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Halodimethylsulfonium halide 1, which is readily formed in situ from hydrohaloic acid and DMSO, is a good nucleophilic halide. This activated nucleophilic halide rapidly converts aryldiazonium salt prepared in situ by the same hydrohaloic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohaloic acid in DMSO is required for the direct transformation of aromatic amines, which results in the production of aryl halides within 1 h. Substituted compounds with electron-donating or -withdrawing groups or sterically hindered aromatic amines are also smoothly transformed to the corresponding aromatic halides. The only observed by-product is the deaminated arene (usually 7%). The isolated aryldiazonium salts can also be converted to the corresponding aryl halides using 1. The present method offers a facile, one-step procedure for transforming aminoarenes to haloarenes and lacks the environmental pollutants that usually accompany the Sandmeyer reaction using copper halides.
- Baik, Woonphil,Luan, Wanqiang,Lee, Hyun Joo,Yoon, Cheol Hun,Koo, Sangho,Kim, Byeong Hyo
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p. 213 - 219
(2007/10/03)
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- Microbial deoxygenation of N-oxides with Baker's yeast-NaOH
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The microbial deoxygenation of a series of aromatic and heteroaromatic N-oxide compounds, including quinoline N-oxides, isoquinoline N-oxides, 2-aryl-2H-benzotriazole 1-oxides, benzo[c]cinnoline N-oxide and azoxybenzenes, has been performed with bakers'yeast-NaOH.
- Baik, Woonphil,Kim, Dong Ik,Koo, Sangho,Rhee, Jong Uk,Shin, Sung Hee,Kim, Byeong Hyo
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p. 845 - 848
(2007/10/03)
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- 1,3-dibromo-5,5-dimethylhydantoin, a useful reagent for aromatic bromination
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1,3-dibromo-5,5-dimethylhydantoin (DBDMH) is a useful and easy to handle reagent for bromination of various aromatic derivatives substituted with electron donating groups. In the presence of trimethylsilyltrifluoromethanesulfonate, DBDMH showed increased reactivity, and in one case, the reaction followed another pathway, suggesting an alternative mechanism.
- Chassaing, Christophe,Haudrechy, Arnaud,Langlois, Yves
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p. 4415 - 4416
(2007/10/03)
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- Bipyridyls and their use as inks
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Process employing bipyridyls as inks, of the general formula STR1 in which R, R' are, for example, alkyl and R1, R2, R3, R4, R5, R6 are, for example hydrogen or alkyl radicals, or R1 and R2 or R2 and R3, and/or R4 and R5 or R5 and R6 together with the pyridine ring form in isoquinoline or quinoline ring system.
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- SYNTHESIS OF 4-ALKOXYQUINOLINES FROM QUINOLINE REISSERT COMPOUNDS
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The quinoline Reissert compound (5a) was converted to 1-benzoyl-3-bromo-2-cyano-1,2,3,4-tetrahydro-4-methoxyquinoline (6a) by successive treatment in methanol with bromine and aq. sodium carbonate.Hydrolysis of 6a with hydrochloric acid gave 3-bromoquinoline (4; R=H), but that with aq. sodium hydroxide afforded 4-methoxyquinoline (7a).Reissert compounds derived from some quinoline derivatives (5) gave the corresponding 4-methoxyquinolines (7) through tetrahydroquinolines (6) in a similar way.
- Sugiura, Michiharu,Sakurai, Yoshie,Hamada, Yoshiki
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p. 561 - 568
(2007/10/02)
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- Substituent effects in the hydrolysis of quinoline-boranes
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Rates of hydrolysis of quinoline-boranes (QB) in aqueous dioxane are dramatically influenced by substitution in both the hetero and all-carbon ring systems. Effects of 3-, 4-, and 6-substituents appear to be due to electronic induction. Rates obtained at 25 °C with 3- and 4-substituted quinoline-boranes correlate with Hammett σm and σp parameters for both acid-independent and acid-catalyzed pathways, which are depicted respectively by k1 and k2 in the expression -d[QB]/dt = [QB](k1 + k2[H+]). Results are consistent with previously proposed mechanisms involving, for the first-order process, dissociative loss of BH3 and, for the acid-catalyzed reaction, electrophilic displacement of BH3 via cis attack of hydrogen ion at nitrogen. Methyl substitution at C-2 enhances k1 presumably through a steric effect and k2 through an inductive effect. A significant steric effect of the peri hydrogen at C-8 is suggested through a comparison of kinetic parameters for substituted quinoline-boranes with those of isoquinoline-borane, wherein k1 may be observed to change by over 4 orders of magnitude. Such substituent effects are significant in the projected synthetic use of heteroaromatic amine-boranes in protic media.
- Minter, David E.,Kelly, Curtis R.,Kelly, Henry C.
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p. 3291 - 3294
(2008/10/08)
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- Novel Pyrethroid Insecticides. II. Synthesis of α-Cyano Substituted 3-Quinolylmethyl Esters
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A new type of pyrethroid insecticides containing quinoline system has been synthesized from the corresponding cyclopropanecarboxylic acid chlorides and α-cyano-3-quinolylmethanol.
- Balicki, Roman,Kozlowska, Margarita,Sobotka, Wieslaw
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p. 281 - 287
(2007/10/02)
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- Process for bromination of pyrimidine
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The process for brominating pyrimidine which comprises reacting bromine at an elevated temperature with the hydrogen halide addition salt of pyrimidine in an organic solvent substantially inert to the action of bromine under the conditions of the process. The process is also shown to be applicable to other nitrogen-containing heterocycles.
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