- A convenient synthetic approach to a novel class of aryldifluoromethyl pyrimidine derivatives containing strobilurin motif as insecticidal agents
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A series of aryldifluoromethyl pyrimidine compounds containing strobilurin were synthesized through bioelectronic isometric design with azoxystrobin as the lead compound and a convenient approach to aryldifluoromethylpyrimidine intermediates was developed, which features mild reaction conditions and simple operation. The title compounds and aryldifluoromethylpyrimidine intermediates were characterized by NMR and HRMS. Both 7c and 7l of the preliminary screening tests showed 100% inhibition against Mythimna separata at 100 mg/L. At 20 mg/L, the lethal rate of 7l against Mythimna separata can be up to 80%.
- Hao, Shulin,Cai, Zengfei,Zhang, Wenliang,Cao, Yangyang,Du, Xiaohua
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- Silver-catalyzed decarboxylative radical allylation of α,α-difluoroarylacetic acids for the construction of CF2-allyl bonds
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An efficient silver-catalyzed method of decarboxylative radical allylation of α,α-difluoroarylacetic acids to build CF2-allyl bonds has been developed. Using allylsulfone as an allyl donor, α,α-difluorine substituted arylacetic acids bearing various functional groups are successfully allylated to access a series of 3-(α,α-difluorobenzyl)-1-propylene compounds in moderate to excellent yields in aqueous CH3CN solution under the mild conditions. Experimental studies disclosed that the α-fluorine substitution of arylacetic acid has a great influence on free radical activity and reactivity.
- Wang, Pingyang,Du, Pengcheng,Sun, Qianqian,Zhang, Jianhua,Deng, Hongmei,Jiang, Haizhen
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supporting information
p. 2023 - 2029
(2021/03/16)
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- Direct Approach to 3-Fluoroindoles and 3,3-Difluoroindolines from 2,2-Difluoro-2-phenylethan-1-amines via C-H/N-H Coupling
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Herein, a direct method for the synthesis of 3-fluoroindoles and 3,3-difluoroindolines from easily accessible 2,2-difluoro-2-phenyl ethan-1-amines is presented. This protocol was performed by Pd-catalyzed direct C-H/N-H coupling and employed picolinamide as a directing group. By controlling the temperature for this transformation, various 3,3-difluoroindolines and 3-fluoroindoles could be isolated with moderate to good yields.
- Zhang, Lanfei,Zhang, Xiaofei,Cui, Yongmei,Yang, Chunhao
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supporting information
p. 3815 - 3826
(2021/06/28)
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- CARBOXY DERIVATIVES WITH ANTIINFLAMMATORY PROPERTIES
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The invention relates to compounds of formula (I) and to their use in treating or preventing an inflammatory disease or a disease associated with an undesirable immune response: (I) wherein, RA1, RA2, RC and RD are as defined herein.
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Page/Page column 111
(2021/07/02)
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- Synthetic method of aromatic ring group or aromatic heterocyclic tetrazole
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The synthetic method comprises the following steps: (1) reacting 1.0 eq of ArI or HArI with 1.2 eq of ethyl 2, 2-difluoroacetate in the presence of DMSO as a solvent and 4.0 eq of Cu under the protection of nitrogen at 30 DEG C and 50 DEG C, and purifying to obtain a first intermediate compound; (2) dissolving 1.0 eq of the first intermediate compound in a mixed solvent of THF and water, adding 2.0 eq of LiOH, reacting at room temperature for 2 hours, spin-drying the solvent, adding HCl until the pH value is equal to 3, and filtering to obtain a second intermediate compound; and (3) reacting 1.0 eq of the second intermediate compound with 2.0 eq of diphenyl azide phosphate in the presence of 2.5 eq of triethylamine by taking tert-butyl alcohol as a solvent to generate aromatic ring group or aromatic heterocyclic tetrazole. The invention provides a novel synthetic method of aromatic ring group or aromatic heterocyclic tetrazole, wherein a target compound can be more conveniently obtained, and reagents participating in the reaction are low in toxicity, mild in reaction condition, simple and safe in aftertreatment, good in product quality and suitable for large-scale production.
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Paragraph 0036-0042; 0052
(2020/12/30)
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- CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE
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Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.
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Paragraph 00234; 00235; 00657; 00658
(2018/07/29)
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- PYRROLOPYRIMIDINE DERIVATIVES AS NR2B NMDA RECEPTOR ANTAGONISTS
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Disclosed are chemical entities of formula I: [INSERT CHEMICAL FORMULA HERE] wherein X, Y, Z, R1, R3, R4, R5 and R6 are defined herein, as NR2B subtype selective receptor antagonists. Also disclosed are pharmaceutical compositions comprising a chemical entity of formula I, and methods of treating various diseases and disorders associated with NR2B antagonism, e.g., diseases and disorders of the CNS, such as depression, by administering a chemical entity of formula I.
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Paragraph 0382
(2016/04/09)
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- TREATMENT OF ANXIETY DISORDERS AND AUTISM SPECTRUM DISORDERS
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Disclosed are methods for treating autism spectrum disorders and/or anxiety disorders by administering certain NR2B subunit-selective NMDA (N methyl-D aspartate) antagonists. Anxiety disorders include agoraphobia (with or without panic disorder), generalized anxiety disorder (GAD), social anxiety disorder (SAD), panic disorder (PD), post-traumatic stress disorder (PTSD) and obsessive-compulsive disorder (OCD).
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Paragraph 0112; 0113
(2016/04/20)
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- Silver-catalyzed oxidative decarboxylation of difluoroacetates: Efficient access to C-CF2 bond formation
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A mild, versatile and efficient method for the silver(i)-catalyzed oxidative decarboxylative gem-difluoromethylenation has been developed. The radical cascade reaction comprises the addition of an oxidatively generated difluoromethylene radical to the isonitrile functionality and subsequent homolytic aromatic substitution. It provides a novel and efficient access to the C-CF2 bond formation.
- Wan, Wen,Ma, Guobin,Li, Jialiang,Chen, Yunrong,Hu, Qingyang,Li, Minjie,Jiang, Haizhen,Deng, Hongmei,Hao, Jian
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p. 1598 - 1601
(2016/01/30)
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- 18F-Labeling of Aryl-SCF3, -OCF3 and -OCHF2 with [18F]Fluoride
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We report that halogenophilic silver(I) triflate permits halogen exchange (halex) nucleophilic 18F-fluorination of aryl-OCHFCl, -OCF2Br and -SCF2Br precursors under mild conditions. This AgI-mediated process allows for the first time access to a range of 18F-labeled aryl-OCHF2, -OCF3 and -SCF3 derivatives, inclusive of [18F]riluzole. The 18F-labeling of these medicinally important motifs expands the radiochemical space available for PET applications. A halogen exchange (halex) 18F-fluorination process offers access for the first time to 18F-labeled arylOCF3, arylOCHF2 and arylSCF3, three motifs of established medicinal importance in PET radiotracers. The use of silver(I) triflate is critical to permit 18F-labeling under mild conditions.
- Khotavivattana, Tanatorn,Verhoog, Stefan,Tredwell, Matthew,Pfeifer, Lukas,Calderwood, Samuel,Wheelhouse, Katherine,Leecollier, Thomas,Gouverneur, Vronique
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supporting information
p. 9991 - 9995
(2015/08/19)
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- Nickel-catalyzed cross-coupling of functionalized difluoromethyl bromides and chlorides with aryl boronic acids: A general method for difluoroalkylated arenes
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Transition-metal-catalyzed difluoroalkylation of aromatics remains challenging despite the importance of difluoroalkylated arenes in medicinal chemistry. Herein, the first successful example of nickel-catalyzed difluoroalkylation of aryl boronic acids is described. The reaction allows access to a variety of functionalized difluoromethyl bromides and chlorides, and paves the way to highly cost-efficient synthesis of a wide range of difluoroalkylated arenes. The notable features of this protocol are its high generality, excellent functional-group compatibility, low-cost nickel-catalyst, and practicality for gram-scale production, thus providing a facile method for applications in drug discovery and development.
- Xiao, Yu-Lan,Guo, Wen-Hao,He, Guo-Zhen,Pan, Qiang,Zhang, Xingang
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supporting information
p. 9909 - 9913,5
(2014/12/09)
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- Palladium-catalyzed difluoroalkylation of aryl boronic acids: A new method for the synthesis of aryldifluoromethylated phosphonates and carboxylic acid derivatives
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The palladium-catalyzed difluoroalkylation of aryl boronic acids with bromodifluoromethylphosphonate, bromodifluoroacetate, and further derivatives has been developed. This method provides a facile and useful access to a series of functionalized difluoromethylated arenes (ArCF2PO(OEt) 2, ArCF2CO2Et, and ArCF2CONR 1R2) that have important applications in drug discovery and development. Preliminary mechanistic studies reveal that a single electron transfer (SET) pathway may be involved in the catalytic cycle. Palladium does it: The palladium-catalyzed difluoroalkylation of aryl boronic acids with bromodifluoromethylphosphonate, bromodifluoroacetate, and further derivatives has been developed (see scheme). Preliminary mechanistic studies reveal that a single electron transfer (SET) pathway may be involved in the catalytic cycle. Copyright
- Feng, Zhang,Min, Qiao-Qiao,Xiao, Yu-Lan,Zhang, Bo,Zhang, Xingang
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supporting information
p. 1669 - 1673
(2014/03/21)
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- Cobalt-catalyzed cross-coupling reaction of arylzinc reagents with ethyl bromodifluoroacetate
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Transition metal-catalyzed cross-coupling reactions of arylmetal reagents with ethyl bromodifluoroacetate have been explored. After intensive investigations, we have successfully found that a cobalt-catalyzed cross-coupling reaction (catalytic alkoxycarbonyldifluoromethylation) of arylzinc reagents with ethyl bromodifluoroacetate smoothly proceeded to afford the corresponding ethyl aryldifluoroacetates in moderate to good yields.
- Araki, Keisuke,Inoue, Munenori
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p. 3913 - 3918
(2013/06/27)
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- &α,&α-Difluoroarylacetic Acids: Preparation from (Diethylamino)sulfur Trifluoride and &α-Oxoarylacetates
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Several α,α-difluoroarylacetic acids have been prepared by reaction of DAST ((diethylamino)sulfur trifluoride) with esters of α-oxoarylacetic acids and then hydrolysis of the resulting difluoro ester.Examples include the α,α-difluoro derivates of the synthetic plant auxin, α-naphthylacetic acid, and the antiinflammatory drug, ibufenac.
- Middleton, W. J.,Bingham, E. M.
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p. 2883 - 2887
(2007/10/02)
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