- 1/10-water maleic acid chlorpheniramine compound and pharmaceutical composition thereof (by machine translation)
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The invention discloses-water 1/10 maleic acid chlorphenamine maleate compound and a preparation method thereof, wherein the compound is measured by a powder X-2 θ ± 0.2° ray diffraction method and shows characteristic 12.4 ° diffraction peaks 18.9 ° 13.1 ° at 20.3 ° 19.4 ° diffraction 21.6 ° 22.0 ° angles in 24.2 ° 24.7 °, 25.1 ° 26.3 ° and 30.1 ° 32.3 °. 1/10 Water prepared by the method has the advantages of good stability, high purity, good solubility and high bioavailability of the preparation, and is simple in process, high in yield, high in repeatability and suitable for industrial production. (by machine translation)
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Paragraph 0042-0043; 0047-0048; 0052-0053
(2020/07/28)
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- A new method for synthesizing of chlorpheniramine maleate (by machine translation)
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The invention belongs to the field of organic synthesis of the drug, in particular to a new synthetic method of chlorpheniramine maleate. The invention comprises the following sequence of steps: (1) under acidic conditions, to [...] in cobalt catalyst, in the presence of a [...] and 2 - halo pyridine react, generating 2 - to the benzylic pyridine; (2) 2 - to the benzylic pyridine in under the action of the sodium amide and N, N - dimethyl base halogen ethane reaction, generating the cream, chlorpheniramine and maleic acid and get chlorpheniramine maleate. The method of reaction steps is relatively short, the raw material is cheap, the process is simple, easy to operate, does not need special reaction conditions, therefore is more suitable for industrial production. (by machine translation)
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Paragraph 0031-0032; 0034-0035
(2019/11/12)
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- Ligand-Free Iridium-Catalyzed Dehydrogenative ortho C?H Borylation of Benzyl-2-Pyridines at Room Temperature
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A convenient and ligand-free iridium-catalyzed dehydrogenative ortho C?H borylation of benzyl-2-pyridines has been developed. The reaction proceeds smoothly at room temperature using pinacolborane as a borylating reagent in the presence of catalytic amount of [IrOMe(COD)]2. The reaction is compatible with many functional groups, providing a vast array of ortho borylated products in moderate to excellent yields with excellent selectivities. (Figure presented.).
- Yang, Yuhuan,Gao, Qian,Xu, Senmiao
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p. 858 - 862
(2019/01/04)
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- Cobalt-Catalyzed Formation of Functionalized Diarylmethanes from Benzylmesylates and Aryl Halides
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A simple cobalt-catalyzed reductive coupling protocol allowing the synthesis of functionalized diarylmethanes from benzyl mesylate is described. The possibility to directly use the benzyl alcohol as a result of a two-step reaction is also presented. This method tolerates a variety of functional groups. A benzyl radical is likely involved. (Figure presented.).
- Reddy, Bhoomireddy Rajendra Prasad,Chowdhury, Sushobhan,Auffrant, Audrey,Gosmini, Corinne
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p. 3026 - 3029
(2018/08/24)
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- Metal-Free Halogen(I) Catalysts for the Oxidation of Aryl(heteroaryl)methanes to Ketones or Esters: Selectivity Control by Halogen Bonding
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Metal-free halogen(I) catalysts were used for the selective oxidation of aryl(heteroaryl)methanes [C(sp3)?H] to ketones [C(sp2)=O] or esters [C(sp3)?O]. The synthesis of ketones was performed with a catalytic amount of NBS in DMSO solvent. Experimental studies and density functional theory (DFT) calculations supported the formation of halogen bonding (XB) between the heteroarene and N-bromosuccinimide, which enabled imine–enamine tautomerism of the substrates. No additional activator was required for this crucial step. Isotope-labeling and other supporting experiments suggested that a Kornblum-type oxidation with DMSO and aerobic oxygenation with molecular oxygen took place simultaneously. A background XB-assisted electron transfer between the heteroarenes and halogen(I) catalysts was responsible for the formation of heterobenzylic radicals and, thus, the aerobic oxygenation. For selective acyloxylation (ester formation), a catalytic amount of iodine was employed with tert-butyl hydroperoxide in aliphatic carboxylic acid solvent. Several control reactions, spectroscopic studies, and Time-Dependent Density Functional Theory (TD–DFT) calculations established the presence of acetyl hypoiodite as an active halogen(I) species in the acetoxylation process. With the help of a selectivity study, for the first time we report that the strength of the XB interaction and the frontier orbital mixing between the substrates and acyl hypoiodites determined the extent of the background electron-transfer process and, thus, the selectivity of the reaction.
- Guha, Somraj,Sekar, Govindasamy
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supporting information
p. 14171 - 14182
(2018/09/10)
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- Photocatalyzed ortho-Alkylation of Pyridine N-Oxides through Alkene Cleavage
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A photocatalyzed reaction of pyridine N-oxides with alkenes gives ortho-alkylated pyridines with cleavage of the carbon–carbon double bond. Benzyl and secondary alkyl groups are incorporated at the ortho position of pyridines in one pot.
- Zhou, Wang,Miura, Tomoya,Murakami, Masahiro
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supporting information
p. 5139 - 5142
(2018/05/30)
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- Copper-Catalyzed Base-Controlled Diastereoselective Synthesis of Tetraarylethanes from 2-Benzylpyridines
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A highly efficient and base-controlled diastereoselective synthesis of tetraarylethanes through copper-catalyzed dehydrogenative homocoupling of readily available 2-benzylpyridines is reported. Various dl - and meso -tetraarylethanes were diastereoseletively synthesized by this new protocol, where base plays the role of the principle modulator: Grignard reagents selectively provide the C2 isomers, whereas KO t -Bu promotes the formation of the meso -tetraarylethanes. Interestingly, the presence of excess KO t -Bu generates the (E)-tetraarylethenes as the only product.
- Chandrasekar, Selvaraj,Karthikeyan, Iyyanar,Sekar, Govindasamy
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p. 1275 - 1283
(2017/12/26)
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- Novel synthetic method for chlorpheniramine maleate
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The invention belongs to the field of medicinal chemistry, and specifically relates to a synthetic method for chlorphenamine maleate. The method provided by the invention comprises the following steps in sequence: (1) allowing p-cyanobenzylchloride to react with acetylene under the catalysis of a catalyst namely cobaltocene so as to generate p-chlorobenzyl pyridine; and (2) allowing p-chlorobenzyl pyridine to react with N,N-dimethyl chloroethane under the catalysis of sodium amide so as to generate chlorpheniramine, and subjecting chlorpheniramine and maleic acid to a neutralization reaction so as to generate chlorpheniramine maleate.
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Paragraph 0016; 0017; 0021; 0022
(2017/07/19)
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- Copper-Catalyzed Aerobic Oxygenation of Benzylpyridine N-Oxides and Subsequent Post-Functionalization
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A copper-catalyzed aerobic oxidation of benzylpyridine N-oxides is reported. The N-oxide moiety acts as a built-in activator for the benzylic methylene oxidation, without requirement of additives. Reaction conditions were identified which suppress undesired benzoylpyridine formation via N-deoxygenation involving intermolecular oxygen transfer. The versatility of the N-oxide group of the benzoylpyridine N-oxide reaction products for post-functionalization of the pyridine ring is demonstrated through efficient C–C, C–N, C–O and C–Cl bond forming procedures, with both nucleophiles and electrophiles. Finally, the applicability of the new synthetic methodology is demonstrated in an alternative route towards the antihistaminic drug Acrivastine via three consecutive N-oxide activated C–H functionalization processes, starting from picoline N-oxide. (Figure presented.).
- Sterckx, Hans,Sambiagio, Carlo,Médran-Navarrete, Vincent,Maes, Bert U. W.
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p. 3226 - 3236
(2017/09/13)
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- Efficient Selenium-Catalyzed Selective C(sp3)?H Oxidation of Benzylpyridines with Molecular Oxygen
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An efficient selenium-catalyzed direct oxidation of benzylpyridines in aqueous DMSO has been successfully developed by using molecular oxygen as the oxidant. A variety of benzoylpyridines with broad functional group tolerance were obtained in modest to excellent yields and with exclusive chemoselectivity. (Figure presented.).
- Jin, Weiwei,Zheng, Poonnapa,Wong, Wing-Tak,Law, Ga-Lai
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supporting information
p. 1588 - 1593
(2017/05/05)
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- Versatile C(sp2)?C(sp3) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes
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The reaction of chiral (hetero)aryl benzyl sulfoxides with Grignard reagents affords enantiomerically pure diarylalkanes in up to 98 % yield and greater than 99.5 % enantiomeric excess. This ligand coupling reaction is tolerant to multiple substitution patterns and provides access to diverse areas of chemical space in three operationally simple steps from commercially available reagents. This strategy provides orthogonal access to electron-deficient heteroaromatic compounds, which are traditionally synthesized by transition metal catalyzed cross-couplings, and circumvents common issues associated with proto-demetalation and β-hydride elimination.
- Dean, William M.,?iau?iulis, Mindaugas,Storr, Thomas E.,Lewis, William,Stockman, Robert A.
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p. 10013 - 10016
(2016/08/16)
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- Palladium-catalyzed decarboxylative couplings of 2-(2-Azaaryl)acetates with aryl halides and triflates
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Pd-catalyzed decarboxylative cross-couplings of 2-(2-azaaryl)acetates with aryl halides and triflates have been discovered. This reaction is potentially useful for the synthesis of some functionalized pyridines, quinolines, pyrazines, benzoxazoles, and benzothiazoles. Theoretical analysis shows that the nitrogen atom at the 2-position of the heteroaromatics directly coordinates to Pd(II) in the decarboxylation transition state.
- Shang, Rui,Yang, Zhi-Wei,Wang, Yan,Zhang, Song-Lin,Liu, Lei
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supporting information; experimental part
p. 14391 - 14393
(2010/12/19)
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- Synthesis of pyridines and pyrazines using an intramolecular hydroamination-based reaction sequence
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A management issue! Various pyridines and pyrazines can be efficiently accessed from simple acyclic precursors using an intramolecular hydroamination/isomerization/aromatization sequence (see scheme). ρ-Toluenesulfonic acid (2 mol%) is used to catalyze this novel alkyne annulation, in which the oxime group allows for a subsequent redoxneutral aromatization step to occur.
- Rizk, Toni,Bilodeau, Eric J.-F.,Beauchemin, Andre M.
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supporting information; experimental part
p. 8325 - 8327
(2010/01/16)
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- LIGAND COUPLING REACTION ON THE PHOSPHORUS ATOM
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Phosphine oxides bearing two or three 2-pyridyl groups were found to react with organometallic compounds affording 2,2'-bipyridyl, 2-substituted pyridines and pyridine in substantial yields.Both ligand exchange and ligand coupling appear to take place within the penta-coordinated phosphorus intermediates formed incipiently.
- Uchida, Yuzuru,Onoue, Katsumi,Tada, Nobuaki,Nagao, Fumio
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p. 567 - 570
(2007/10/02)
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- SENSITIVE NATURE OF LIGAND COUPLING AND PSEUDOROTATION TO ELECTRONIC EFFECT OF SUBSTITUENT---LIGAND COUPLING IN THE REACTIONS OF BENZYLIC ARYL SULFOXIDES WITH BENZYLIC GRIGNARD REAGENTS
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Unlike the reaction of benzylic 2-pyridyl sulfoxides with benzylic Grignard reagents, in the reaction of p-benzenesulfonylphenyl benzylic sulfoxides with benzylic Grignard reagents, benzylic groups bearing an electronwithdrawing group tends to couple with the aryl group preferentially.This change is considered to be due to a slight change of electronic environements which would effect on the ease of pseudorotation of the incipient ?-sulfurane formed during the reaction.
- Wakabayashi, Shoji,Ishida, Masahiro,Takeda, Takashi,Oae, Shigeru
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p. 4441 - 4444
(2007/10/02)
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- Method of regulating the growth of aquatic weeds with pyridine derivatives
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A method of regulating the growth of submerged and floating aquatic weeds which comprises adding a 2- or 4-substituted pyridinemethane or pyridinemethanol to a body of water containing the submerged and floating aquatic weeds to be regulated, in quantities sufficient to regulate the growth of the submerged and floating aquatic weeds therein. The disclosure also relates to novel compositions for carrying out the method.
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