cas 524-38-9, N-Hydroxyphthalimide | Articles data

Articles about 524-38-9Total 55 be found

Article title
Article abstract
Author
Journal number and time
Download

Reactivity of phthalimide N-oxyl radical (PINO) toward the phenolic O-H bond. A kinetic study
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.
Baciocchi, Enrico,Gerini, Maria Francesca,Lanzalunga, Osvaldo
p. 8963 - 8966
(2004)
Read Online

A Catalyst-Free Synthesis of Fused Perfluoroalkylated 2,3-Dihydroisoxazoles via Oxa-Michael-Aldol Annulation
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.
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)

Synthesis, Crystal Structure, Herbicidal Activity, and SAR Study of Novel N-(Arylmethoxy)-2-chloronicotinamides Derived from Nicotinic Acid
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
p. 6423 - 6430
(2021/06/28)

N-(benzyloxy)-2-chloronicotinamide compound as well as preparation method and application thereof
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.
-
Paragraph 0016; 0026-0028

(2021/06/23)

Synthesis method N -hydroxyphthalimide
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.
-
Paragraph 0015-0022

(2021/09/15)

Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains
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.
Akunuri, Ravikumar,Veerareddy, Vaishnavi,Kaul, Grace,Akhir, Abdul,Unnissa, Tanveer,Parupalli, Ramulu,Madhavi,Chopra, Sidharth,Nanduri, Srinivas
supporting information

(2021/08/27)

Ring opening of N-hydroxyphthalimide to construct phenylurea derivatives
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.
Wu, Yinhui,Lv, Bin,Zhang, Yanan,Gao, Pan,Zhang, Min,Yuan, Yu
supporting information
p. 2025 - 2033
(2021/05/29)

Me3SI-promoted chemoselective deacetylation: a general and mild protocol
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.
Gurawa, Aakanksha,Kashyap, Sudhir,Kumar, Manoj
p. 19310 - 19315
(2021/06/03)

Preparation method of isoxazolidine hydrochloride
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.
-
Paragraph 0035; 0039; 0040

(2020/07/13)

N-benzyloxy substituted symmetric oxamide compound and preparation method and application thereof
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.
-
Paragraph 0029; 0033-0034

(2020/12/30)

KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot
A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is
Gurawa, Aakanksha,Kumar, Manoj,Rao, Dodla S.,Kashyap, Sudhir
supporting information
p. 16702 - 16707
(2020/10/27)

Metal-Free C(sp3)-H Allylation via Aryl Carboxyl Radicals Enabled by Donor-Acceptor Complex
The first aryl carboxyl radical generation by the donor-acceptor complex with N-acyloxyphthalimides and Hantzsch esters is reported. Regio- and chemoselective C(sp3)-H bond allylation is enabled by aryl carboxyl radicals with visible light irradiation under mild and metal-free conditions.
Li, Yang,Zhang, Jing,Li, Defang,Chen, Yiyun
supporting information
p. 3296 - 3299
(2018/06/11)

A mild system for synthesis of aldoximes and ketoximes in the presence of N-hydroxyphthalimide in aqueous system
An efficient method for synthesis of oximes from aldehydes or ketones with N-hydroxyphthalimide or N-hydroxysuccinimide in water has been described. It is the first time to utilize NHPI as an oximation reagent to synthesize aldoximes and ketoximes from the corresponding organic carbonyl compounds without other reagents. The reaction tolerates various functional groups and affords the corresponding oximes in 76%–98% yields. The by-product phthalic acid can be recycled from the system. In addition, this method has been successfully applied to the synthesis of the precursor of some pharmacologically active amide molecules.
Jiang, Xiaoying,Xu, Xiaohe,Lin, Yuyan,Yan, Yiyan,Li, Pingping,Bai, Renren,Xie, Yuanyuan
supporting information
p. 5879 - 5885
(2018/09/06)

PRODUCTION OF CYCLIC IMIDES SUITABLE FOR OXIDATION CATALYSIS
Disclosed are novel processes for the production of cyclic imide compounds such as N-hydroxyphthalimide (NHPI). The processes may be particularly well-suited for commercial-scale production of cyclic imides such as NHPI. Such cyclic imide compounds are suitable for use as oxidation catalysts, and specifically may be used to oxidize cyclohexylbenzene to cyclohexyl-1-phenyl-1-hydroperoxide. Such an oxidation may be particularly useful in a process for the production of phenol and/or cyclohexanone from benzene via a process comprising hydroalkylation of benzene to cyclohexylbenzene, oxidation of the cyclohexylbenzene to cyclohexyl-1-phenyl-1-hydroperoxide, and cleavage of the cyclohexyl-1-phenyl-1-hydroperoxide to phenol and cyclohexanone. The cyclic imide production process may advantageously include water washing and reactant recovery steps to maximize purity and yield.
-
Paragraph 00104-00110

(2017/12/29)

A N - hydroxy phthalic acid imide preparation method (by machine translation)
The invention relates to a N - hydroxy phthalic acid imide preparation method, comprises the following steps: (1) the phthalic anhydride and hydrochloric acid in the hydroxylamine is added to the isopropyl alcohol; (2) then add triethylamine, for 70 - 95 °C lower, reaction 0.5 - 1.5 h, reduced pressure distillation recovery isopropyl alcohol and triethylamine, then washing, and dried to obtain the N - hydroxy phthalimide. The advantage of this invention is mainly embodied in: uses the isopropanol as a new reaction medium, and the use of triethylamine as the accelerator, not only reduces the solvent toxicity, improves the safety of the reaction, purification energy consumption is reduced, but also shortens the reaction time, and high product purity. In addition promoter triethylamine compared with the inorganic salt and ferric oxide purification process more simple and easy to operate, is very suitable for industrial production. (by machine translation)
-
Paragraph 0022; 0024; 0025; 0026; 0028

(2017/09/12)

Fmoc-OPhth, the reagent of Fmoc protection
Fmoc-OSu has been widely used for Fmoc protection of amino groups, especially amino acids, in solid phase peptide synthesis. However, it has been recognized that Fmoc-βAla-OH is formed as a by-product via the Lossen rearrangement during the reaction. Since we reconfirmed the formation of Fmoc-βAla-OH during the preparation of Fmoc-AA-OH by Fmoc-OSu, Fmoc-OPhth was designed and synthesized as a new Fmoc reagent to avoid the formation of Fmoc-βAla-OH. Furthermore, Fmoc protection by Fmoc-OPhth and Fmoc-SPPS were evaluated. The various Fmoc-amino acids prepared by Fmoc-OPhth were carried out in good yields and these are applicable in Fmoc-SPPS.
Yoshino, Ryo,Tokairin, Yoshinori,Kikuchi, Mari,Konno, Hiroyuki
supporting information
p. 1600 - 1603
(2017/04/03)

Hydrogen Atom Transfer (HAT) Processes Promoted by the Quinolinimide-N-oxyl Radical. A Kinetic and Theoretical Study
A kinetic study of the hydrogen atom transfer (HAT) reactions from a series of organic compounds to the quinolinimide-N-oxyl radical (QINO) was performed in CH3CN. The HAT rate constants are significantly higher than those observed with the phthalimide-N-oxyl radical (PINO) as a result of enthalpic and polar effects due to the presence of the N-heteroaromatic ring in QINO. The relevance of polar effects is supported by theoretical calculations conducted for the reactions of the two N-oxyl radicals with toluene, which indicate that the HAT process is characterized by a significant degree of charge transfer permitted by the π-stacking that occurs between the toluene and the N-oxyl aromatic rings in the transition state structures. An increase in the HAT reactivity of QINO was observed in the presence of 0.15 M HClO4 and 0.15 M Mg(ClO4)2 due to the protonation or complexation with the Lewis acid of the pyridine nitrogen that leads to a further decrease in the electron density in the N-oxyl radical. These results fully support the use of N-hydroxyquinolinimide as a convenient substitute for N-hydroxyphthalimide in the catalytic aerobic oxidations of aliphatic hydrocarbons characterized by relatively high C-H bond dissociation energies.
Dilabio, Gino A.,Franchi, Paola,Lanzalunga, Osvaldo,Lapi, Andrea,Lucarini, Fiorella,Lucarini, Marco,Mazzonna, Marco,Prasad, Viki Kumar,Ticconi, Barbara
p. 6133 - 6141
(2017/06/23)

A novel histone deacetylase inhibitors
The invention belongs to the field of medical chemistry, and particularly relates to a novel histone deacetylase inhibitor and a preparation method thereof, a pharmaceutical combination containing the histone deacetylase inhibitor, and application of the inhibitor in preparing drugs for preventing and/or treating diseases related to histone deacetylase activity out-of-control (especially antitumor application).
-
Paragraph 0075; 0076

(2018/01/11)

Synthetic process of O-3-chloro-2-propenyl hydroxylamine
The invention belongs to the technical field of organic synthesis, in particular relates to a synthetic process of O-3-chloro-2-propenyl hydroxylamine. The synthetic process comprises the following steps of (1) successively adding phthalic acid and thionyl chloride into a reactor, performing a temperature rising reaction, distilling and removing excessive thionyl chloride to obtain o-phthaloyl chloride; (2) dissolving hydroxylamine hydrochloride into dichloromethane, dropwise adding the o-phthaloyl chloride, continually stirring and reacting after dropwise adding, distilling and removing the dichloromethane after reaction completion, so as to obtain N-hydroxyl phathalicimide; (3) dissolving the N-hydroxyl phathalicimide into a sodium hydroxide aqueous solution, dropwise adding trans-1,3-dichloropropene for reaction, after reaction completion, filtering to obtain 2-(3-chloroallyloxy)-isopropyl indolizine-1,3-dione; (4) adding the 2-(3-chloroallyloxy)-isopropyl indolizine-1,3-dione into a hydrochloric acid solution for hydrolysis, filtering, collecting organic phases, and the O-3-chloro-2-propenyl hydroxylamine is obtained. The synthetic process provided by the invention has the advantages that raw materials are low in price and easy to obtain, the reaction condition is mild and the yield is high.
-
Paragraph 0046

(2016/10/09)

Synthesis of 3,5-isoxazolidinediones and 1 H -2,3-benzoxazine-1,4(3 H)-diones from aliphatic oximes and dicarboxylic acid chlorides
The synthesis of the title compounds was carried out by reacting dicarboxylic acid chlorides with oximes in the presence of excess triethylamine. Disubstituted malonyl chlorides gave 2-alkenyl-4,4-dialkyl-3,5- isoxazolidinediones (8a-f) and 2,2′-ethylidene-bis[4,4-dialkyl-3,5- isoxazolidinedione]s (9a-f). Compounds 9 were formed from 8 and its N-unsubstituted 3,5-isoxazolidinedione decomposition product. Phthaloyl chlorides reacted with acetone oxime to yield 3-(1-methylethenyl)-1H-2,3- benzoxazine-1,4(3H)-diones (16a-e). Products 16 spontaneously decomposed to give N-unsubstituted 1H-2,3-benzoxazine-1,4(3H)-diones (17a-e) at rates that were dependent on temperature and solvent. Kinetic studies showed that two of the compounds decomposed by zero-order kinetics under neutral conditions. Butanedioyl chloride did not produce a cyclic product.
Izydore, Robert A.,Jones, Joseph T.,Mogesa, Benjamin,Swain, Ira N.,Davis-Ward, Ronda G.,Daniels, Dwayne L.,Kpakima, Felicia Frazier,Spaulding-Phifer, Sharnelle T.
p. 2874 - 2882
(2014/05/06)

Versatile and sustainable synthesis of cyclic imides from dicarboxylic acids and amines by Nb2O5 as a base-tolerant heterogeneous lewis acid catalyst
Catalytic condensation of dicarboxylics acid and amines without excess amount of activating reagents is the most atom-efficient but unprecedented synthetic method of cyclic imides. Here we present the first general catalytic method, proceeding selectively and efficiently in the presence of a commercial Nb2O5 as a reusable and base-tolerant heterogeneous Lewis acid catalyst. The method is effective for the direct synthesis of pharmaceutically or industrially important cyclic imides, such as phensuximide, N-hydroxyphthalimide (NHPI), and unsubstituted cyclic imides from dicarboxylic acid or anhydrides with amines, hydroxylamine, or ammonia.
Ali, Md. Ayub,Siddiki, S. M. A. Hakim,Kon, Kenichi,Hasegawa, Junya,Shimizu, Kenichi
supporting information
p. 14256 - 14260
(2015/01/09)

C-H bond functionalization with the formation of a C-C bond: A free radical condensation reaction based on the phthalimido-N-oxyl radical
The development of a new chemical process that effects the conversion RH + C=C-C-X → R-C-C=C + HX, in which X is the phthalimido-N-oxyl radical (PINO·), is reported. The reaction yields are high, mass balances are excellent, and C-H bond functionalization and C-C bond formation are achieved in a single transformation. The byproduct of the reaction, N-hydroxyphthalimide, precipitates from solution and can be easily removed by simple filtration (and recycled). The kinetic chain lengths are shorter and the reaction times are longer (relative to those of the analogous reactions of allyl bromides), most likely because PINO· is a less-reactive hydrogen-atom abstractor. There appears to be no significant difference in efficiency in the addition-elimination steps. Competition experiments reveal that Br· and PINO· are comparable in leaving group ability. The introduction of a new chain carrier, the phthalimido-N-oxyl radical (PINO·), leads to an improved chain reaction. This chain reaction is successful and high reaction yields are reported for the functionalization of hydrocarbons. Kinetic studies reveal that this reaction is an efficient chain process, and the leaving group ability of PINO · is comparable to that of Br·. Copyright
Patil, Shradha,Chen, Liang,Tanko, James M.
p. 502 - 505
(2014/02/14)

Formation of C-O bond via cross-dehydrogenative coupling between isochroman and oxime under metal-free oxidation conditions
DDQ-mediated C-O bond formation through cross-dehydrogenative coupling (CDC) reaction without any metal catalyst under mild conditions was developed. Series of isochromans and oximes could be employed as substrates, and the products were obtained in good yields. Georg Thieme Verlag Stuttgart New York.
He, Hua-Feng,Wang, Kai,Xing, Bo,Sheng, Guorong,Ma, Tingxuan,Bao, Weiliang
supporting information
p. 211 - 214
(2013/03/13)

Synthesis and Antimicrobial Activities of Oximes Derived from O- Benzylhydroxylamine as FabH Inhibitors
Forty-three oxime derivatives were synthesized by allowing O-benzylhydroxylamines to react with primary benzaldehydes or salicylaldehydes; these products were gauged as potential inhibitors of β-ketoacyl-(acyl-carrier-protein) synthaseIII (FabH). Among the 43 compounds, 38 are reported herein for the first time. These compounds were assayed for antimicrobial activities against Escherichia coli, Pseudomonas aeruginosa, Pseudomonas fluorescens, Bacillus subtilis, Staphylococcus aureus, and Enterococcus faecalis. Compounds with prominent antibacterial activities were tested for their E. coli FabH inhibitory activities. 3-((2,4 Dichlorobenzyloxyimino) methyl) benzaldehyde O-2,4-dichlorobenzyl oxime (44) showed the best antibacterial activity, with minimum inhibitory concentrations of 3.13-6.25μgmL-1 against the tested bacterial strains, exhibiting the best E. coli FabH inhibitory activity, with an IC50 value of 1.7mM. Docking simulations were performed to position compound 44 into the E. coli FabH active site in order to determine the most probable binding conformation.
Luo, Yin,Zhang, Li-Rong,Hu, Yang,Zhang, Shuai,Wang, Xiao-Ming,Zhu, Hai-Liang,Fu, Jie
p. 1587 - 1593,7
(2020/08/31)

AGONISTS OF GPR40
The present invention relates to compounds that have the ability to modulate the activity of GPR40 and are there-fore useful in the treatment of GPR40 related disorders. In addition the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders related to GPR40 activity.
-
Page/Page column 175-176

(2012/02/05)

One-pot synthesis and luminescent spectra of 3-allyl substituted quinazoline-2,4-dione derivatives as allyl capping agents
3-Nitro-N-(phenylsulphonyloxy)phthalimide (IIIa) and N-(phenylsulphonyloxy) phthalimide (IIIb) were synthesised as key intermediates in good yield. Their structures were confirmed by 1H NMR and FTIR spectral data. The reaction of the key intermediates with allylamine produced 3-allyl-5- nitroquinazoline-2,4-(1H,3H)-dione (IVa) and 3-allylquinazoline-2,4-(1H,3H)- dione (IVb), respectively. Luminescence emission and excitation spectra of IVa and IVb are also presented.
Farouk, Mahmoud,Alrokayan, Salman A.,Imran, Ahamad,Abu-Salah, Khalid M.
body text
p. 75 - 78
(2012/04/04)

Synthesis, biological evaluation, and molecular docking studies of 2,6-dinitro-4-(trifluoromethyl)phenoxysalicylaldoxime derivatives as novel antitubulin agents
A series of 2,6-dinitro-4-(trifluoromethyl)phenoxysalicylaldoxime derivatives (1h-20h) have been designed and synthesized, and their biological activities were also evaluated as potential antiproliferation and tubulin polymerization inhibitors. Among all the compounds, 2h showed the most potent activity in vitro, which inhibited the growth of MCF-7, Hep-G2 and A549 cell lines with IC50 values of 0.70 ± 0.05, 0.68 ± 0.02 and 0.86 ± 0.05 μM, respectively. Compound 2h also exhibited significant tubulin polymerization inhibitory activity (IC50 = 3.06 ± 0.05 μM). The result of flow cytometry (FCM) demonstrated that compound 2h induced cell apoptosis. Docking simulation was performed to insert compound 2h into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. Based on the preliminary results, compound 2h with potent inhibitory activity in tumor growth may be a potential anticancer agent.
Zhao, Ting-Ting,Lu, Xiang,Yang, Xian-Hui,Wang, Li-Ming,Li, Xi,Wang, Zhong-Chang,Gong, Hai-Bin,Zhu, Hai-Liang
experimental part
p. 3233 - 3241
(2012/07/14)

Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs
A series of novel analogs of pyrrole alkaloid were designed and synthesized by a facile method and their structures were characterized by 1H NMR, 13C NMR and high-resolution mass spectrometry (HRMS). The structure of compound 2a was identified by 2D NMR including heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC) and H-H correlation spectrometry (H-H COSY) spectra. Their antifungal activities against five fungi were evaluated, and the results indicated that some of the title compounds showed moderate fungicidal activities in vitro against Alternaria solani, Cercospora arachidicola, Fusarium omysporum, Gibberella zeae and Physalospora piricola at the dosage of 50 μg mL -1. Compound 2a and 3a exhibited good activities against P. piricola at low dosage.
Wang, Ming-Zhong,Xu, Han,Liu, Tuan-Wei,Feng, Qi,Yu, Shu-Jing,Wang, Su-Hua,Li, Zheng-Ming
scheme or table
p. 1463 - 1472
(2011/05/04)

Synthesis of some N,N-diemoxyphmalimido-5-(substitutedphenyl)-3-methyl-1, 3a, 4, 5-tetrahydropyrazolo[3,4-c] pyrazole-4-spiro-5-substituted-1H-indole-2- one
5-Methyl-2,4-dihydro-3H-pyrazol-3-one reacts with isatin 1a, b in ethanol to give a solid product, On addition of warm benzene, one part (benzene soluble) is 4a, b and another part (benzene insoluble) is 2a, b, Compounds 3, 5-dimethyl-4, 7-dihydro-1H-pyrazolo[4', 3': 5, 6]pyrano[2, 3c]pyrazole-4-spiro- 5-substituted-1H-indole-2-one 2a, b on treatment with bromo-ethoxyphthalimide in DMF yield N, N, N-triethoxyphthalimido-3, 5-dimethyl-4, 7-dihydro- 1H-pyrazolo [4', 3; 5, 6]pyrano[2, 3-c]pyrazole-4-spiro-5-substituted-1H-indole-2-one 3a, b, 3-(3-Methyl-5-oxo-1, 5-dihydro-4H-pyrazol-4-ylidene)-1, 3-dihydro-2H-indol-2- one 4a, b are converted to corresponding pyrazolopyrazole derivatives 5a-f by reaction with substituted phenyl hydrazine, These are finally condensed with bromoethoxyphthalimide in DMF and pyridine as a base to give titled compounds N, N-diethoxyphthalimido-5-(substituted phenyl )-3-methyl-1, 3a, 4, 5-tetrahydropyrazolo[3, 4-c]pyrazole-4-spiro-5-substituted-1H-indole-2-one 6a-f, The structures of all the synthesized compounds are supported by spectral and analytical data.
Hussain, Nasir,Dangi, Rajaram,Sharma, Chirag Kumar,Talesara, Ganpat Lai
scheme or table
p. 885 - 889
(2011/08/09)

PROCESS FOR PREPARING N-SUBSTITUTED CYCLIC IMIDES
In a process for making an N-substituted phthalimide compound, an amine is contacted with a carboxylic acid anhydride and allowed to react in an aqueous solution at a pH of about 2 to about 6. Optionally, the reactants are combined with an acid to lower the pH of the reaction solution wherein the lowering of the pH optimizes the yield of the desired N-substituted phthalimide product. The N-substituted phthalimide may be, for example, N- hydroxyphthalimide, and the reactants may be phthalic anhydride and hydroxylamine or a salt thereof. The N-substituted phthalimide compound is useful for, among other things, the oxidation of various hydrocarbons.
-
Page/Page column 11-12

(2010/11/04)

Synthetic and biological studies on some fused pyrazoles and their ethoxyphthalimide derivatives
Ethylacetoacetate reacts with nicotinohydrazide in absolute ethanol to give 5-methyl-2-(pyridin-3-ylcarbonyl)-2, 4-dihydro- 3H-pyrazol-3-one 1 which upon condensation with various aryl aldehydes affords the related arylidene derivatives 3a-d. Cyclisation reaction between hydrazine hydrate and compounds 3a-d yields l-nicotinoyl-3-methyl-4-(4-substituted phenyl)-3a, 4- dihydro pyrazolo[3, 4-c]pyrazoles 4a-d. Subsequently title compounds 6a-d are obtained by reaction between compounds 4a-d and phthalimidoxy ethyl bromide 5 in presence of base. Final compounds have been screened for various cell cultures of antimicrobial and antiviral testing with various expand standard drugs.
Joshi, Ajit,Sain, Devendra K.,Thadhaney, Bhawana,Ojha, Swati,Hussain, Nasir,Talesara, Ganpat L.
scheme or table
p. 965 - 970
(2010/10/18)

Synthesis of α-chloropyridine-containing oximes of 3β,5-dihydroxy-6-ketosteroids
New derivatives of steroidal 6-ketoximes containing α-chloropyridine neonicotinoid groups characteristic of bioactive compounds were synthesized by formation of oximes of cholestane and stigmastane 3β,5-dihydroxy-6- ketosteroids with O-(2-chloropyridin-5-ylmethyl)hydroxylamine in the presence of zinc or tin(IV) chloride.
Kovganko,Sokolov,Chernov,Kashkan,Survilo
body text
p. 750 - 755
(2011/02/22)

Synthesis of some 1-{2-(phthalimido-N-oxy)-ethyl} derivatives of 4-(4-substituted phenyl)-2,6-dimethyl-1,4-dihydro-3,5-bis-N-4-oxo-2- phenylquinazolin-3(4H)-ylcarboxamides
A series of 1-{2-(phthalimido-N-oxy)-ethyl}-4-(4-substituted phenyl)-2,6-dimelhyl-1,4-dihydro-3,5-bis-N-(4-oxo-2-phenylquinazolin-3(4H) -ylcarboxamides (6a-d) have been synthesized via a multistep reaction sequence. Ethyl acetoacetate, various araldehydes and aminonia were condensed in ethanol to yield diethyl 4-(4-substituted phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5- dicarboxylate (2a-d). Ester group of these 2a-d was replaced by hydrazine hydrate in dioxane to give 4-(4-substituted phenyl)-2,6-dimethyl-1,4- dihydropyridine-3,5-dicarbohydrazide (3a-d). These were further treated with benzoxazine-4(3H)-one to give 4-(4-substituted phenyl)-2,6-dimethyl-1,4-dihydro- 3,5-bis-N-(4-oxo-2-phenylquinazolin-3(4H)-ylcarboxamides (4a-d). Final compounds 6a-d were obtained by refluxing 4a-d with bromoethoxyphthalimide (5). The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, 1H NMR and mass spectral data.
Dangi, Raja Ram,Hussain, Nasir,Sain, Devendra Kumar,Talesara
scheme or table
p. 1409 - 1414
(2011/09/20)

Synthesis of some novel ethoxyphthalimide derivatives of pyrazolo[3,4-c]pyrazoles
The synthesis of 5-methyl-4-substituted benzylidene-2,4-dihydro-3H-pyrazol- 3-one 3a-d is achieved by the condensation reaction of 5-methyl-2,4-dihydro-3H- pyrazol-3-one 1 with 4-substituted benzaldehydes 2a-d. Compound 1 is prepared by the cyclization reaction between ethylacetoacetate and hydrazine hydrate in absolute alcohol. Compounds 3a-d are converted into corresponding ethoxyphthalimide derivatives 5a-d by treatment with phthalimidoxyethyl bromide 4. 1-N-Ethoxyphthlimido-3-methyl-4-(4-substituted benzylidene)pyrazol-5-ones 5a-d are reacted with thiosemicarbazide/NaOH and isoniazid/AcONa/AcOH separately to yield 6-N-ethoxyphthalimido-4-methyl-3-(4-substituted phenyl)-2- thiocarbamoyl-3,3α-dihydro pyrazolo[3,4-c]pyrazoles 6a-d and 6-N-ethoxyphthalimido-2-isonicotinoyl-4-methyl-3-(4-substituted phenyl)-3,3α-dihydro pyrazolo[3,4-c]pyrazoles 7a-d respectively. Structures of the synthesized compounds have been elucidated by means of IR, 1H NMR and mass spectral data.
Sharma, Chirag,Thadhaney, Bhawana,Pemawat, Gangotri,Ltalesara
scheme or table
p. 1892 - 1897
(2009/05/09)

Microwave-assisted synthesis of N-hydroxyphthalimide derivatives
N-Hydroxyphthalimide derivatives are readily obtained in good yields by the reaction of phthalic anhydrides with hydroxylamine hydrochloride in the presence of pyridine under microwave irradiation.
Sugamoto, Kazuhiro,Matsushita, Yoh-Ichi,Kameda, Yu-Hei,Suzuki, Masahiko,Matsui, Takanao
p. 67 - 70
(2007/10/03)

Synthesis and antibacterial evaluation of some theophylline derivatives
Some novel antiasthmatic theophylline derivatives have been synthesized and evaluated for biological activity. Oxygen substituted hydroxylamine compounds have been found to possess versatile pharmacological activities. Theophylline N-alkoxyarylbiguanides 8a-d have been prepared by condensing corresponding N-alkoxyamine salt 6a-c with substituted aryldicyandiamide 7, which in turn is prepared by Gabriel hydrolysis of corresponding alkoxyphthalimides 5a-c. Theophylline is converted to its sodium salt using sodium hydride and treated with bromoalkoxy phthalimide in DMF media. In an another attempt N-allyl theophylline 9 is brominated and condensed with double mole ratio of N-hydroxyphthalimide to obtain 2,3-bis-oxyphthalimido-1-theophylline propane 11. Majority of these compounds have been screened for their antimicrobial activity.
Rathore, Kavita,Vyas, Ritu,Talesara
p. 2166 - 2170
(2007/10/03)

Electron-transfer mechanism in the N-demethylation of N,N-dimethylanilines by the phthalimide-N-oxyl radical
The reactivity of the phthalimide N-oxyl radical (PINO) toward the N-methyl C-H bond of a number of 4-X-substituted N,N-dimethylanilines (X = OMe, OPh, CF3, CO2Et, CN) has been investigated by product and kinetic analysis. PINO was generated in CH3CN by reaction of N-hydroxyphthalimide (NHPI) with Pb(OAc)4 or, for the kinetic study of the most reactive substrates (X = OMe, OPh), with tert-butoxyl radical produced by 266 nm laser flash photolysis of di-tert-butyl peroxide. The reaction was found to lead to the N-demethylation of the N,N-dimethylaniline with a rate very sensitive to the electron donating power of the substituent (ρ+ = -2.5) as well as to the oxidation potential of the substrates. With appropriately deuterated N,N-dimethylanilines the intermolecular and intramolecular deuterium kinetic isotope effects (DKIEs) were measured for some substrates (X = OMe, CO2Et, CN) with the following results. First, intramolecular DKIE [(kH/kD) intra] was found to be always different and higher than intermolecular DKIE [(kH/kD)inter]; second, no intermolecular DKIE [(kH/kD)inter = 1] was observed for X = OMe, whereas substantial values of (kH/k D)inter were exhibited by X = CO2Et (4.8) and X = CN (5.8). These results, while are incompatible with a single step hydrogen atom transfer from the N-C-H bond to the N-oxyl radical, as proposed for the reaction of PINO with benzylic C-H bonds, can be nicely interpreted on the basis of a two-step mechanism involving a reversible electron transfer from the aniline to PINO leading to an anilinium radical cation, followed by a proton-transfer step that produces an α-amino carbon radical. In line with this conclusion the reactivity data exhibited a good fit with the Marcus equation and a λ value of 37.6 kcal mol-1 was calculated for the reorganization energy required in this electron-transfer process. From this value, a quite high reorganization energy (> 60 kcal mol-1) is estimated for the PINO/NHPI(-H)- self-exchange reaction. It is suggested that the N-demethylated product derives from the reaction of the α-amino carbon radical with PINO to form either a cross-coupling product or an α-amino carbocation. Both species may react with the small amounts of H2O present in the medium to form a carbinolamine that, again by hydrolysis, can be eventually converted into the N-demethylated product.
Baciocchi, Enrico,Bietti, Massimo,Gerini, Maria Francesca,Lanzalunga, Osvaldo
p. 5144 - 5149
(2007/10/03)

Kinetics of self-decomposition and hydrogen atom transfer reactions of substituted phthalimide N-oxyl radicals in acetic acid
(Chemical Equation Presented). Kinetic data have been obtained for three distinct types of reactions of phthalimide N-oxyl radicals (PINO ?) and N-hydroxyphthalimide (NHPI) derivatives. The first is the self-decomposition of PINO? wh
Cai, Yang,Koshino, Nobuyoshi,Saha, Basudeb,Espenson, James H.
p. 238 - 243
(2007/10/03)

Suggested improved method for the Ing-Manske and related reactions for the second step of gabriel synthesis of primary amines
This work demonstrates an improvement in the Ing-Manske and related procedures by the increase of pH of the reaction mixture after the complete disappearance of N-substituted phthalimide. Hydrazinolysis of N-phenylphthalimide (1a) gave 80% of the desired primary amines after 5.3 h in the absence of added NaOH. The reaction time was reduced to 1.6 h and 1.2 h when 1 eq. and 5eq. of NaOH were added to the reaction mixture after the complete disappearance of 1a. Hydroxyaminolysis of N-(4-ethylphenyl)phthalimide (1b) gave 80% of the desired primary amines after 7.5 h of reaction time (at added [NaOH] = 0). When 10 eq. and 20 eq. of NaOH were added to the reaction mixture after the disappearance of Ib, the reaction time was reduced to 4 h and 2 h, respectively. Methylaminolysis of N-(2-ethylphenyl)phthalimide (1c) gave 80% of the desired primary amines after 1.7 h (at added [NaOH] = 0). The reaction time was reduced to 1 h and 0.7 h when 1 eq. and 25 eq. of NaOH were added to the reaction mixture after the complete disappearance of 1c.
Ariffin, Azhar,Khan, Mohammad Niyaz,Lan, Lai Chwee,May, Fan Yen,Yun, Chien Siew
p. 4439 - 4445
(2007/10/03)

Dual linker with a reference cleavage site for information rich analysis of polymer-supported transformations
Two dual linker systems with specific reference cleavage sites were designed and synthesized to accelerate and simplify development and optimization of reaction conditions for solid-phase synthesis. The dual linker allows simple evaluation of cleavage rate of polymer-supported compounds from the linker and, at the same time, ensures that all resin-bound components are cleaved from the solid support. The dual linker 4 was assembled from two Wang linkers connected by a three carbon spacer. The linker 9 was synthesized using the PAL and HMPB linkers.
Krchňák, Viktor,Slough, Greg A.
p. 5237 - 5241
(2007/10/03)

Kinetic Study of the Phthalimide N-Oxyl Radical in Acetic Acid. Hydrogen Abstraction from Substituted Toluenes, Benzaldehydes, and Benzyl Alcohols
The phthalimide N-oxyl (PINO) radical was generated by the oxidation of N-hydroxyphthalimide (NHPI) with Pb(OAc)4 in acetic acid. The molar absorptivity of PINO. is 1.36 × 103 L mol -1 cm-1 at λmax 382 nm. The PINO radical decomposes slowly with a second-order rate constant of 0.6 ± 0.1 L mol-1 s-1 at 25°C. The reactions of PINO . with substituted toluenes, benzaldehydes, and benzyl alcohols were investigated under an argon atmosphere. The second-order rate constants were correlated by means of a Hammett analysis. The reactions with toluenes and benzyl alcohols have better correlations with σ+ (ρ = -1.3 and -0.41), and the reaction with benzaldehydes correlates better with σ (ρ = -0.91). The kinetic isotope effect was also studied and significantly large values of kH/kD were obtained: 25.0 (p-xylene), 27. 1 (toluene), 27.5 (benzaldehyde), and 16.9 (benzyl alcohol) at 25°C. From the Arrhenius plot for the reactions with p-xylene and p-xylene-d10, the difference of the activation energies, EaD - E aH, was 12.6 ± 0.8 kJ mol-1 and the ratio of preexponential factors, AH/AD, was 0.17 ± 0.05. These findings indicate that quantum mechanical tunneling plays an important role in these reactions.
Koshino, Nobuyoshi,Saha, Basudeb,Espenson, James H.
p. 9364 - 9370
(2007/10/03)

Monomer having electron-withdrawing group and process for preparing the same
A monomer containing an electron-withdrawing group of the present invention is represented by following Formula (a), (b) or (c): wherein A1, A2, and A3 are each a ring; Ra, Rb, Rc, and Ru are the same or different and are each a hydrogen atom or organic group; at least one of Rs, Rw and Rv, at least one of Rt and Rw1, and at least one of the two Rw2s are each an electron-withdrawing group, and the others are each a hydrogen atom or organic group; W1 is a single bond or linkage group; and n denotes an integer of 2 to 25, where at least two of Ra, Rb, Rc, Rs, Rt, Ru, Rv, Rw, Rw1, Rw2, W1, and carbon atoms constituting ring A1, carbon atoms constituting ring A2, and carbon atoms constituting ring A3 may be combined to form a ring, respectively. The electron-withdrawing groups in Rs, Rt, Rv, Rw, Rw1, and Rw2 are, for example, groups each containing a fluorine atom. The monomer is useful as a raw material for photoresist polymeric compounds.
-
(2008/06/13)

Method of separating imide compound
A reaction product and an imide compound can be separated from a reaction mixture obtained by reacting a substrate in the presence of the imide compound having an imide unit represented by the following formula (1): wherein X represents an oxygen atom, a hydroxyl group or an acyloxy group by (A1) a solvent-crystallization step for crystallizing the imide compound with at least one solvent selected from the group consisting of a hydrocarbon, a chain ether and water, (A2) a cooling-crystallization step for crystallizing the reaction product by cooling, or (B) an extraction step for distributing the reaction product into a phase of a water-insoluble solvent and the imide compound into a phase of an aqueous solvent, respectively by using the aqueous solvent containing at least water and the water-insoluble solvent separable from the aqueous solvent. Further, the imide compound and the metal catalyst can be separated from a mixture containing the imide compound and the metal catalyst by (C) a solvent-crystallization step for crystallizing the imide compound by using a solvent for crystallization, (D) an absorption step for absorbing the metal catalyst by an absorption treatment, or (E) an extraction step for distributing the imide compound into a phase of a water-insoluble solvent and the metal catalyst into a phase of an aqueous solvent, respectively by using the aqueous solvent containing at least water and the water-insoluble solvent separable from the aqueous solvent.
-
(2008/06/13)

Process for the preparation of cyclic N-hydroxydicarboximides
The invention discloses a process for the preparation of cyclic N-hydroxydicarboximides, involving reacting a dicarboxylic acid or anhydride thereof with a salt of hydroxylamine in solution without the further addition of a base.
-
(2008/06/13)

Mild and convenient one pot synthesis of N-hydroxyimides from N-unsubstituted imides
A new, one pot synthesis of various N-hydroxyimides from N-unsubstituted imides is described. Imides are first transformed into their N-Boc derivatives, which are next reacted with aqueous hydroxylamine, providing crystalline hydroxylammonium salts of the corresponding N-hydroxyimides. Filtration and acidic workup affords pure N-hydroxyimides.
Einhorn,Einhorn,Marcadal-Abbadi
p. 741 - 748
(2007/10/03)

Process for the preparation of aldehydes and ketones
A process for the preparation of vinyl, alkynyl or aryl aldehydes or vinyl, alkynyl or aryl ketones includes reacting vinyl-, alkynyl- and aryl- and -methylene compounds with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, heterocyclic or aromatic NO or NOH containing compounds.
-
(2008/06/13)

Intermediates for making HIV-protease inhibitors
HIV protease inhibitors inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds can be prepared by the novel methods of the present invention using the novel inventive intermediates.
-
(2008/06/13)

Intermediates for making HIV-protease inhibitors
HIV protease inhibitors inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds can be prepared by the novel methods of the present invention using the novel inventive intermediates.
-
(2008/06/13)

Reaction of 1-hydroxyphthalimide derivatives with aluminum chloride in benzene
The reaction of 1-hydroxyphthalimide derivatives with AlCl3 in benzene has been investigated. From 1-hydroxyphthalimide (1a) 2-hydroxy-3,3-diphenyl-2,3-dihydroisoindol-1-one (2) and 1,1-diphenyl-1H-benzo[d][1,2]oxazm-4-one (3) are obtained by initial attack of benzene on the imide carbonyl, assisted by the neighboring oxygen atom. Heating 2 with Lewis acid (Alcl3) in benzene results in ring expansion to afford 3, while heating 3 with protic acid (H2SO4) leads to ring contraction to give 2. From O-(2-phenethyl)- and O-benzoyl derivatives (1b and c), 1,2-diphenylethane (4) and benzophenone (5) are obtained, respectively, by the heterolytic cleavage of an C-O bond.
Uto, Kensaku,Sakamoto, Takeshi,Matsumoto, Keita,Kikugawa, Yasuo
p. 633 - 640
(2007/10/03)

Nucleophilic reactions of N-hydroxy-,methoxy-,2,3-epoxypropoxy-phthalimides
Reaction of N-hydroxyphthalimide (4) with equivalent amounts of aliphatic and aromatic primary amines gives the N-substituted phthalimides (7), while with excess of these amines if gives the diamides (8) of phthalic acid.The reaction of 4 with t-butyl amine gives only the butyl monoamide (9a) of phthaloylhydroxamic acid.N-Methoxyphthalimide (5) reacts in the same manner.Compound 4 does not condense with epichlorohydrin, but condense with epibromohydrin to give N-(2,3-epoxypropoxy)phthalimide (6) which on reaction with equivalent amounts of aliphatic primary amines gives the N-substituted phthalimides (7) and with excess of the amines it gives the diamides (8) of phthalic acid.The reaction of 6 with aromatic primary amines gives only the N-arylphthalimides.Secondary amines do not react with 6.
Ranadive, V. B.,Khadilkar, B. M.,Samant, S. D.
p. 1175 - 1177
(2007/10/02)