- N-(benzyloxy)-2-chloronicotinamide compound as well as preparation method and application thereof
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The invention belongs to the technical field of chemical synthesis and medicine application, and particularly relates to preparation and application of an N-(benzyloxy)-2-chloronicotinamide compound. The preparation method comprises the following steps: reacting phthalic anhydride with hydroxylamine, then reacting with triethylamine for acidification to prepare N-hydroxyphthalimide, then carrying out substitution and hydrazinolysis, and finally reacting with dichloronicotinoyl chloride to prepare the N-(benzyloxy)-2-chloronicotinamide compound. The preparation method disclosed by the invention is simple and convenient to operate, the structure of the obtained product is confirmed by a nuclear magnetic hydrogen spectrum, herbicidal activity tests are carried out on the obtained 15 target products, and results show that all target compounds have an obvious inhibition effect on the seeds of the Agrostis matsumurae under the concentration of 1mM, and the inhibition effect reaches 100%; and along with the decrease of the concentration, even if the concentration reaches 100 [mu] M, the target compound can still show good herbicidal activity.
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Paragraph 0016; 0035-0036
(2021/06/23)
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- Synthesis, Crystal Structure, Herbicidal Activity, and SAR Study of Novel N-(Arylmethoxy)-2-chloronicotinamides Derived from Nicotinic Acid
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Nicotinic acid, also known as niacin, is a natural product, which is widely found in plants and animals. To discover novel natural-product-based herbicides, a series of N-(arylmethoxy)-2-chloronicotinamides were designed and synthesized. Some of the new N-(arylmethoxy)-2-chloronicotinamides exhibited excellent herbicidal activity against Agrostis stolonifera (bentgrass) at 100 μM. Compound 5f (2-chloro-N-((3,4-dichlorobenzyl)oxy)nicotinamide) possessed excellent herbicidal activity against Lemna paucicostata (duckweed), with an IC50 value of 7.8 μM, whereas the commercial herbicides clomazone and propanil had values of 125 and 2 μM, respectively. The structure-activity relationships reported in this paper could be used for the development of new herbicides against monocotyledonous weeds.
- Yu, Chen-Sheng,Wang, Qiao,Bajsa-Hirschel, Joanna,Cantrell, Charles L.,Duke, Stephen O.,Liu, Xing-Hai
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p. 6423 - 6430
(2021/06/28)
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- Ultrasound accelerated synthesis of: O-alkylated hydroximides under solvent- A nd metal-free conditions
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A novel, sustainable, environmentally friendly, high substrate scope, efficient, solvent-free and metal catalyst-free method for the cross-dehydrogenative coupling (CDC) reaction between N-hydroxyphthalimide (NHPI) and benzyl/ether compounds is described. This coupling reaction proceeds through ultrasound acceleration. Compared to conventional heating conditions, the use of ultrasound techniques not only improves the reaction efficiency and enhances the reaction rate but also minimizes the side reactions.
- Jiang, Hongmei,Tang, Xiaoyue,Liu, Sihan,Wang, Lian,Shen, Haicheng,Yang, Jiankui,Wang, Huixian,Gui, Qing-Wen
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p. 10223 - 10227
(2019/12/26)
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- O-benzyl-N-(9-acridinyl)hydroxylamines
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A series of O-benzyl-N-(9-acridinyl)hydroxylamines was prepared, isolated, and evaluated for biological activity using both thermal denaturation and MTT assays. Changes in the thermal denaturation temperature of genomic calf-thymus DNA ranged from +6.6 °C to +20.2 °C. MTT assays on SNB-19 glioblastoma cells provided biological activity that ranged from 17.4 μM to 33.2 μM. Both evaluation methods of biological activity indicate that substitution of the benzyl group by either electron-withdrawing or electron-donating groups provides a measureable benefit in these assays. The two assays agreed on the magnitude of the interaction for each substitution pattern.
- Johnson, Alyssa L.,Duncan, Nathan,Mosher, Michael D.
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p. 139 - 148
(2018/06/27)
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- Method for preparing PINO (phthimide-n-oxyl) derivatives through directly coupling NHPI (n-hydroxyphthalimide)and benzyl-containing compounds under non-metal catalysis
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The invention discloses a method for preparing PINO (phthimide-n-oxyl) derivatives through directly coupling NHPI (n-hydroxyphthalimide) and benzyl-containing compounds under non-metal catalysis. According to the method, under the nitrogen protection, the
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Paragraph 0040; 0041; 0045 - 0047; 0060 - 0062
(2017/04/22)
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- Catalytic ortho -acetoxylation of masked benzyl alcohols via an exo -directing mode
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A Pd-catalyzed ortho-acetoxylation of masked benzyl alcohols to synthesize various 2-hydroxyalkylphenol derivatives is reported. The 2,6-dimethoxyl benzaldoxime proved to be an efficient exo-type directing group for arene (sp2) C-H functionalization. Two strategies were demonstrated to remove the directing group through N-O and C-O bond cleavages. A high catalyst turnover (>1000) was obtained to illustrate the practicality of this method.
- Ren, Zhi,Schulz, Jonathan E.,Dong, Guangbin
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supporting information
p. 2696 - 2699
(2015/06/16)
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- NBu4NI-catalyzed intermolecular C-O cross-coupling reactions: Synthesis of alkyloxyamines
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A practical and simple nBu4NI-catalyzed C-O bond formation for the synthesis of alkyloxyamines was achieved under metal-free conditions. The reaction is applicable to the coupling of a range of benzylic and allylic hydrocarbons with N-hydroxyphthalimide and is tolerant of various functional groups. The reaction mechanism was primarily investigated and a radical process was proposed.
- Lv, Yunhe,Sun, Kai,Wang, Tingting,Li, Gang,Pu, Weiya,Chai, Nannan,Shen, Huihui,Wu, Yingtao
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p. 72142 - 72145
(2015/09/08)
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- Organocatalytic Radical Involved Oxidative Cross-Coupling of N-Hydroxyphthalimide with Benzylic and Allylic Hydrocarbons
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The cross-coupling reaction between N-hydroxyphthalimide and various benzylic and allylic hydrocarbons was realized through an organocatalytic radical-mediated process involving C(sp3)-O bond formation using tert-butyl hydroperoxide (t-BuOOH) as an oxidant and tetra-n-butylammonium iodide [(n-Bu]4NI] as a catalyst, during which the phthalimide N-oxyl (PINO) radical and benzylic and allylic radicals were generated in situ and underwent the selective radical/radical cross-coupling reaction. This novel method provides a convenient metal-free approach to the synthesis of O-alkylated hydroxy imides under mild reaction conditions.
- Dian, Longyang,Wang, Sisi,Zhang-Negrerie, Daisy,Du, Yunfei
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supporting information
p. 3836 - 3842
(2016/01/25)
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- Generation and cross-coupling of benzyl and phthalimide-N-oxyl radicals in a cerium(IV) ammonium nitrate/N-hydroxyphthalimide/ArCH2R system
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A method was developed for the cross-dehydrogenative coupling of alkylarenes and related compounds with N-hydroxyphthalimide (NHPI) using cerium(IV) ammonium nitrate (CAN) to prepare O-substituted NHPI derivatives. The characteristic feature of the reaction is that NHPI plays a dual role. Thus, in the presence of CAN, NHPI generates the phthalimide-N-oxyl (PINO) radical, which abstracts a hydrogen atom from the benzyl position to form a C-centered radical. The target oxidative cross-coupling product is formed mainly through the recombination of PINO with the C-centered radical. Therefore, NHPI serves as a mediator for the radical process and a reagent for the radical cross-coupling. The target products were obtained in yields from 35 to 80%.
- Terent'ev, Alexander O.,Krylov, Igor B.,Sharipov, Mikhail Y.,Kazanskaya, Zoya M.,Nikishin, Gennady I.
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p. 10263 - 10271,9
(2012/12/12)
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- 1-Benzyloxy-4,5-dihydro-1H-imidazol-2-yl-amines, a novel class of NR1/2B subtype selective NMDA receptor antagonists
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Screening of the Roche compound depository led to the identification of (1-benzyloxy-4,5-dihydro-1H-imidazol-2-yl)-butyl amine 4, a structurally novel NR1/2B subtype selective NMDA receptor antagonist. The structure-activity relationships developed in this series resulted in the discovery of a novel class of potent and selective NMDA receptor blockers displaying activity in vivo.
- Alanine, Alexander,Bourson, Anne,Buettelmann, Bernd,Gill, Ramanjit,Heitz, Marie-Paule,Mutel, Vincent,Pinard, Emmanuel,Trube, Gerhard,Wyler, Rene
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p. 3155 - 3159
(2007/10/03)
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