25062-46-8Relevant articles and documents
Preparation method O - alkyl substituted hydroxylamine salt
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Paragraph 0118; 0124-0127, (2021/11/14)
The invention relates to a preparation method of N - alkyl substituted hydroxylamine salt, and belongs to fine chemical engineering. Pesticide or bulk pharmaceutical chemicals technical field. The present invention reacts with the N - alkyl of the oxime with an inorganic salt of hydroxylamine to give N - alkyl-substituted hydroxylamine salt and oxime. The invention provides an efficient and environment-friendly method for preparing N - alkyl substituted hydroxylamine salt, and simultaneously, an N - alkyl substituted hydroxylamine salt is prepared, and the oxime can be re-prepared to form N - alkylate of oxime so as to realize the material circulation. No equivalent acid is used in the reaction process. Alkali neutralization, avoided the current method to use a large amount of acid, alkali and produce inorganic salt solid waste shortcoming, environmental protection more. The preparation method is mild in reaction condition, and the defects of high pollution and high energy consumption of the traditional process are overcome. In-flight R1 , R2 What is R is as claimed in the claims and the description.
Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3)?H Bonds**
Murugesan, Kathiravan,Donabauer, Karsten,K?nig, Burkhard
supporting information, p. 2439 - 2445 (2020/12/07)
The metal-free activation of C(sp3)?H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug molecules (celecoxib) and complex structures such as l-menthol, amino acids, and cholesterol derivatives. Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcohols and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.
The local and natural sources in synthetic methods: the practical synthesis of aryl oximes from aryl aldehydes under catalyst-free conditions in mineral water
Goksu, H.,Orhan, E.
, (2021/07/27)
The synthesis of oximes from aryl aldehydes was prepared using hydroxylamine hydrochloride. The obtained oxime compounds were synthesized at maximum efficiency in mineral water at room temperature. The developed method is economical, practical and environmentally friendly. All of the aldehydes were converted the oxime a method using local sources and useful for industrial applications is introduced in the literature. Graphic abstract: In this study, addition elimination reaction, one of the important reactions of organic chemistry, was carried out using local sources. With this reaction, aryl oximes were obtained from aryl aldehydes in mineral water under catalyst-free conditions.[Figure not available: see fulltext.]
Design and synthesis of sinomenine isoxazole derivatives via 1,3-dipolar cycloaddition reaction
Pan, Hongmei,Lu, Tong,Wu, Xuedan,Gu, Chengwen,Tao, Naili,Zhang, Biao,Wang, Ao,Chen, Guangmei,Zhang, Kehua,Cheng, Jie,Jin, Jie
supporting information, p. 2360 - 2364 (2019/11/11)
A novel structure of sinomenine isoxazole derivatives is synthesised from sinomenine hydrochloride and aromatic aldehydes and requires six steps. 19 target compounds have been obtained in good yields. The sinomenine hydrochloride transforms to 4-alkynyl sinomenine, which is a key intermediate product to synthesise the target sinomenine isoxazole compounds, after a neutralisation reaction with ammonia and substitution reaction with 3-chloropropyne. Another key intermediate product is 1,3-dipole, which can be obtained from aromatic aldehyde. After treatment with hydroxylamine hydrochloride and then sodium carbonate solution, aromatic aldehyde is converted to aldehyde oxime, which reacts with N-chlorosuccinimide (NCS) to afford aryl hydroximino chloride. 1,3-Dipole is eventually formed in situ while triethylamine (TEA) in DMF is added dropwise. Then 4-alkynyl sinomenine is added to provide the sinomenine isoxazole derivative via 1,3-dipolar cycloaddition reaction as the key step. All the target compounds are characterised by melting point, 1H NMR, 13C NMR, HRMS and FT-IR spectroscopy.
Visible-light mediated stereospecific C(sp2)-H difluoroalkylation of (Z)-aldoximes
Chen, Hua,Deng, Hongmei,Gong, Haiying,Hao, Jian,Li, Mingjie,Peng, Yi,Wan, Wen,Wang, Qian,Zhang, Yifang
supporting information, p. 7867 - 7874 (2021/09/28)
A visible light mediated stereospecific C(sp2)-H difluoroalkylation of (Z)-aldoximes to (E)-difluoroalkylated ketoximes has been described. In this reaction, (hetero)-aromatic and aliphatic difluoroalkylated ketoximes could be obtained with the retention of the configuration of the starting aldoximes. A preliminary mechanism study showed that a difluoromethyl radicalviaan SET pathway was involved.
Lysophosphatidic acid receptor antagonists and preparation method thereof
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Paragraph 0300-0301; 0303-0305, (2020/07/29)
The invention belongs to the technical field of medicinal chemistry, and particularly relates to lysophosphatidic acid receptor antagonists and a preparation method thereof. The applicant surprisinglyfinds that compounds provided by the invention have high LPAR1 antagonistic activity and selectivity, low toxicity, good metabolic stability and good drug development prospect, and can be used for preventing or treating diseases or symptoms related to LPAR1. The applicant also accidentally finds that the IC50 value of part of the compounds can be as low as 300 nM or below and even 50 nM or below.Moreover, the compounds disclosed by the invention have better safety, and the CC50 range of the compounds can reach 200 [mu]M or above. In addition, the compounds of the present invention have goodmetabolic stability in humans, rats, and mice, such excellent inhibitory activity being very desirable for their use as LPAR1 inhibitors in the above diseases or disorders. In addition, the preparation method of the compounds is simple, mild in reaction condition, high in product yield and suitable for industrial production.
CARDIAC SARCOMERE INHIBITORS
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Paragraph 0260, (2020/01/24)
Provided are compounds of Formula (I): or a pharmaceutically acceptable salt thereof, wherein R1, R2, Y1, Y2, L1, and G1 are as defined herein. Also provided is a pharmaceutically acceptable composition comprising a compound of Formula (I), or a pharmaceutically acceptable salt thereof. Also provided are methods of using a compound of Formula (I), or a pharmaceutically acceptable salt thereof.
Synthesis and SAR study of simple aryl oximes and nitrofuranyl derivatives with potent activity against Mycobacterium tuberculosis
Calixto, Stephane Lima,Carvalho, Guilherme da Silva Louren?o,Coimbra, Elaine Soares,Granato, Juliana da Trindade,Louren?o, Maria Cristina da Silva,Wardell, James,da Costa, Cristiane Fran?a,de Souza, Marcus Vinicius Nora
, p. 12 - 20 (2020/02/06)
Background: Oximes and nitrofuranyl derivatives are particularly important compounds in medicinal chemistry. Thus, many researchers have been reported to possess antibacterial, antiparasitic, insecticidal and fungicidal activities. Methods: In this work, we report the synthesis and the biological activity against Mycobacterium tuberculosis H37RV of a series of fifty aryl oximes, ArCH=N-OH, I, and eight nitrofuranyl compounds, 2-nitrofuranyl-X, II. Results: Among the oximes, I: Ar = 2-OH-4-OH, 42, and I: Ar = 5-nitrofuranyl, 46, possessed the best activity at 3.74 and 32.0 μM, respectively. Also, 46, the nitrofuran compounds, II; X = MeO, 55, and II: X = NHCH2Ph, 58, (14.6 and 12.6 μM, respectively), exhibited excellent biological activities and were non-cytotoxic. Conclusion: The compound 55 showed a selectivity index of 9.85. Further antibacterial tests were performed with compound 55 which was inactive against Enterococcus faecalis, Klebisiella pneumonae, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhymurium and Shigel-la flexneri. This study adds important information to the rational design of new lead anti-TB drugs. Structure-activity Relationship (SAR) is reported.
Microwave synthesis method of benzaldoxime compounds
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Paragraph 0060-0063, (2020/12/08)
The invention discloses a microwave synthesis method of benzaldoxime compounds. The method comprises the following steps: dissolving a substituted benzaldehyde, hydroxylamine hydrochloride and an alkaline compound in an organic solvent, placing the formed solution in a microwave reaction kettle for a reaction, spin-drying the solvent after the reaction is finished, conducting mixed extraction withethyl acetate and water, separating an organic phase, carrying out drying with anhydrous sodium sulfate, and successively performing filtering and desolventizing to obtain a benzaldoxime compound. Based on the structure of the substituted benzaldehyde, the substituted benzaldoxime compound is obtained by reacting the aldehyde with hydroxylamine hydrochloride in the microwave reaction kettle. Themethod is simple in process, convenient to operate, short in reaction time and high in yield, meets the requirement for environment friendliness and improves economic benefits.
Cu(II)–metformin immobilized on graphene oxide: an efficient and recyclable catalyst for the Beckmann rearrangement
Solaiman Hamed, Ahmed,Mohammad Ali, Ehab
, p. 701 - 714 (2019/11/03)
Abstract: In this study, for the first time, the copper(II) nanoparticles (NPs) have been immobilized on metformin-functionalized graphene oxide and then its catalytic applications have been investigated in synthesis of amides from aldoximes (Beckmann rearrangement). The chemical structure of prepared catalyst has been characterized by various analyses like FT-IR, TGA, TEM, SEM, EDX, and ICP. All analyses confirm the successful and stable immobilization of copper NPs on functionalized graphene oxide. This synthesized heterogeneous nanocatalyst showed excellent catalytic activity with high product yields and short reaction times. Also, the suggested catalyst could be recycled ten times without a drastic decrease in its catalytic activity. Graphic abstract: [Figure not available: see fulltext.].
