524-38-9Relevant academic research and scientific papers
Reactivity of phthalimide N-oxyl radical (PINO) toward the phenolic O-H bond. A kinetic study
Baciocchi, Enrico,Gerini, Maria Francesca,Lanzalunga, Osvaldo
, p. 8963 - 8966 (2004)
The reactivity of the phthalimide N-oxyl radical (PINO) toward the OH bond of a series of substituted phenols was kinetically investigated in CH 3CN. The reaction selectivity and the deuterium kinetic isotope effect were determined. Information on the kinetic solvent effect was also obtained with phenol as the substrate.
A Catalyst-Free Synthesis of Fused Perfluoroalkylated 2,3-Dihydroisoxazoles via Oxa-Michael-Aldol Annulation
Zhou, Wei,Yao, Lan,Liu, Yongxiurong,Shen, Lichun,Chen, Jie,Deng, Hongmei,Shao, Min,Zhang, Hui,Tang, Xiaojun,Cao, Weiguo
supporting information, p. 429 - 438 (2021/10/01)
A novel synthesis of fused perfluoroalkylated 2,3-dihydroisoxazoles is achieved via oxa-Michael-aldol annulation between perfluoroalk- 2-ynoates and N-hydroxyimides. This method provides a convenient route for the synthesis of pyrrolidin-2-one-fused perfluoroalkylated 2,3-dihydroisoxazoles in yields of up to 97%. Diverse and pharmaceutically attractive polycyclic scaffolds can be obtained rapidly and efficiently under these mild, catalyst-free conditions.
Synthesis, Crystal Structure, Herbicidal Activity, and SAR Study of Novel N-(Arylmethoxy)-2-chloronicotinamides Derived from Nicotinic Acid
Yu, Chen-Sheng,Wang, Qiao,Bajsa-Hirschel, Joanna,Cantrell, Charles L.,Duke, Stephen O.,Liu, Xing-Hai
, p. 6423 - 6430 (2021/06/28)
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.
N-(benzyloxy)-2-chloronicotinamide compound as well as preparation method and application thereof
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Paragraph 0016; 0026-0028, (2021/06/23)
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.
Synthesis method N -hydroxyphthalimide
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Paragraph 0015-0022, (2021/09/15)
The invention discloses a synthesis method of N -hydroxyphthalimide. The reaction is carried out by reflux dehydration and dehydrochlorination in a high boiling point inert solvent by taking phthalic anhydride and hydroxylamine hydrochloride as raw materials, and N - hydroxyphthalimide is obtained in a high yield after the reaction is finished. The molar yield can reach above 98%, and the purity of the product reaches 99% or above. Compared with the prior art, the high-boiling-point inert solvent replaces a traditional water or dioxane aqueous solution as a solvent, so that a large amount of waste water generated is avoided. Pollution emission is reduced, production efficiency is improved, conversion rate is increased, and atom utilization rate is saved.
Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains
Akunuri, Ravikumar,Veerareddy, Vaishnavi,Kaul, Grace,Akhir, Abdul,Unnissa, Tanveer,Parupalli, Ramulu,Madhavi,Chopra, Sidharth,Nanduri, Srinivas
supporting information, (2021/08/27)
Infections caused due to multidrug resistant organisms have emerged as a constant menace to human health. Even though numerous antibiotics are currently available for treating infectious diseases, a great number of bacterial strains have acquired resistance to many of them. Among these, infections caused due to Staphylococcus aureus are predominant in adult and paediatric population. Indole is a prominent chemical scaffold found in many pharmacologically active natural products and synthetic drugs. A number of oxime ether containing compounds have attracted attention of researchers owing to their interesting biological properties. Current work details the synthesis of indole containing oxime ether derivatives and their evaluation for antimicrobial activity against a panel of bacterial and mycobacterial strains. Synthesized compounds demonstrated good to moderate activity against drug-resistant S. aureus including resistant to vancomycin. Among all, compound 5h was found to possess potent activity against susceptible as well as MRSA and VRSA strains of S. aureus with MIC of 1 μg/mL and 2–4 μg/mL respectively. In addition, compound 5h was found to be non-toxic to Vero cells and exhibited good selectivity index of >40. Further, 5h, E-9a and E-9b possessed good biofilm inhibition against S. aureus. With these assuring biological properties, synthesized compounds could be potential prospective antimicrobial agents.
Ring opening of N-hydroxyphthalimide to construct phenylurea derivatives
Wu, Yinhui,Lv, Bin,Zhang, Yanan,Gao, Pan,Zhang, Min,Yuan, Yu
supporting information, p. 2025 - 2033 (2021/05/29)
Arylurea and their analogues have been one of the most ubiquitous backbone during the past century, and extensive studies have been conducted to establish practical synthetic methods for their derivatives. In particular, it is an effective pathway to synthesize arylureas by using commercially available phthalimide compounds. Reported herein is a triethoxyphosphine promoted ring-opening of the N-hydroxyphthalimide (NHPI) by the nucleophilic attack of amines. This transformation shows a wide range of functional-group tolerance under mild reaction conditions.
Me3SI-promoted chemoselective deacetylation: a general and mild protocol
Gurawa, Aakanksha,Kashyap, Sudhir,Kumar, Manoj
, p. 19310 - 19315 (2021/06/03)
A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.
N-benzyloxy substituted symmetric oxamide compound and preparation method and application thereof
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Paragraph 0029; 0033-0034, (2020/12/30)
The invention discloses an N-benzyloxy substituted symmetric oxamide compound and a preparation method and application thereof, the structural formula of the N-benzyloxy substituted symmetric oxamidecompound is shown as the formula (I): in the formula (I), the structures of two substituted benzene rings are the same, the number of substituents R on each substituted benzene ring is 1-2, and the substituent R is selected from H, halogen, C1-C4 alkyl or C1-C3 alkoxy. The N-benzyloxy substituted symmetric oxamide compound is a new compound with an efficient weeding effect, and provides a basis for research and development of a novel herbicide.
Preparation method of isoxazolidine hydrochloride
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Paragraph 0035; 0039; 0040, (2020/07/13)
The invention belongs to the field of organic synthesis, discloses a new route and a new method for preparing a herbicide intermediate, and particularly relates to a preparation method of isoxazolidine hydrochloride. The preparation method comprises the following steps: subjecting N-hydroxyphthalimide and 1-bromo-3-chloropropane to a condensation reaction in the presence of a solvent A and an acid-binding agent; reacting the condensation product that is 2-(3-chloropropoxy) isoindole-1,3-diketone with hydrochloric acid to obtain the isoxazolidine hydrochloride. The 1-bromo-3-chloropropane is adopted in place of 1,3-dichloropropane, the content and the reaction yield of the isoxazolidine hydrochloride prepared in a proper solvent are higher than those of isoxazolidine hydrochloride preparedby a traditional method, and meanwhile, the byproduct phthalic acid can be recycled. In addition, the post-reaction treatment is simpler, so that the product loss is less. Therefore, the production energy consumption is well controlled, the pollution to the environment is reduced, and the reaction safety is improved.
