cas 7386-21-2, N-(4-CHLOROPHENYL)PHTHALIMIDE

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Solvent-free, Efficient Transamidation of Carboxamides with Amines Catalyzed by Recyclable Sulfated Polyborate Catalyst
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Mali, Anil S.,Indalkar, Krishna,Chaturbhuj, Ganesh U.
p. 369 - 378
(2021/07/26)

“On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides
An efficient nano-Cu2O-catalyzed cascade multicomponent reaction of 2-halobenzoic acids and trimethylsilyl cyanide with diverse amines was developed using water as a solvent, affording versatileN-substituted phthalimide derivatives in moderate to excellent yields. This novel strategy features carbon monoxide gas-free, environmentally benign, one-pot multistep transformation, commercially available reagents, a cheap catalyst without any additives, wide functional group tolerance, and operational convenience.
Wen, Xiaowei,Liu, Xiaojuan,Yang, Zhiqi,Xie, Menglan,Liu, Yuxi,Long, Lipeng,Chen, Zhengwang
supporting information
p. 1738 - 1743
(2021/03/14)

Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes
In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of N-iodophthalimide under visible-light irradiation.
Kuribara, Takahito,Nakajima, Masaya,Nemoto, Tetsuhiro
supporting information
p. 2235 - 2239
(2020/03/13)

Method for constructing N-(4-chlorophenyl)phthalimide in one step by using imine as starting material
The invention discloses a method for constructing N-(4-chlorophenyl)phthalimide in one step by using an imine as a starting material. (E)-N-(4-chlorophenyl)-1-phenylmethylenimine used as a reaction raw material undergoes a carbonylation reaction to form t
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Paragraph 0022-0054

(2019/02/13)

PPh3/I2/HCOOH: An efficient CO source for the synthesis of phthalimides
A straightforward and general method has been developed for the synthesis of phthalimide derivatives from 2-iodobenzamides and PPh3/I2/HCOOH in the presence of a catalytic amount of Pd(OAc)2. The reaction results demonstrate that PPh3/I2/HCOOH is a facile, efficient and safe CO source. The whole process is carried out in toluene at 80 °C and furnishes the desired products in good to excellent yields.
Wang, Yingying,Zhou, Yang,Lei, Min,Hou, Jinjun,Jin, Qinghao,Guo, Dean,Wu, Wanying
p. 1180 - 1185
(2019/01/26)

Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides
We report on cyclic imides as weak directing groups for selective monohydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp2)-H bond enabling five-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp2)-H bond via larger six-membered ruthenacycle intermediates. Furthermore, monohydroxylated products were exclusively obtained (even in the presence of overstoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate coplanar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.
Yuan, Yu-Chao,Bruneau, Christian,Dorcet, Vincent,Roisnel, Thierry,Gramage-Doria, Rafael
p. 1898 - 1907
(2019/02/05)

Palladium Catalyzed Regioselective Synthesis of Substituted Biaryl Amides through Decarbonylative Arylation of Phthalimides
The Pd(OAc)2 catalyzed cross-coupling of N-substituted phthalimides with aryl halide provides a single step direct access of a wide range of synthetically appealing ortho-substituted biarylamides in high yields through unique carbonyl (CO) replacement. The reaction proceeds through a ligand-free condition and is well tolerant to the diverse functionality of both imide and halide units. The reaction negates any requirement of organometallic reagent and needs a shorter reaction time and comparatively lower temperature as required for previously reported decarbonylative processes.
Samanta, Partha Kumar,Biswas, Papu
p. 3968 - 3976
(2019/03/26)

Synthesis, molecular docking, cytotoxicity and antioxidant activity evaluation of isoindoline-1,3-dione derivatives
A variety of amines have been employed to functionalize isobenzofuran-1,3-dione to obtain isoindoline-1,3-dione derivatives in the base free conditions. All the synthesized compounds are screened for their bioactivity through molecular docking, cytotoxicity (against HeLa) and antioxidant activity. ABTS and DPPH are employed to assess the antioxidant activity. Among the synthesized isoindoline-1,3-dione derivatives (3a-k), compound 3e has showed the best antioxidant activity and also exhibited better binding energy when docked with caspase-3 protein. Cytotoxicity of the synthesized compounds was studied against cervical cancer cell line (HeLa) and compound 3e has displayed better activity than other isoindoline derivatives.
Kumar, Palanichamy Santhosh,Kumar, Kuruba Bharath,Obadiah, Asir,Kumar, Suluvoy Jagadish,Mohanapriya, Raman,Durairaj, Arulappan,Ramanathan, Subramanian,Vasanthkumar, Samuel
p. 2548 - 2556
(2019/10/02)

Br?nsted acid mediated intramolecular cyclopropane ring expansion/[4 + 2]-cycloaddition
A cascade reaction of 3-hydroxy-2-phenylisoindolin-1-one and cyclopropyl ketone has been developed via a Br?nsted acid-promoted ring-opening/intramolecular cross-cycloaddition/[4 + 2]-cycloaddition process. The developed methodology provides straightforward access to pentacyclic isoindolin-1-one derivatives under simple reaction conditions.
Li, Jian,Zhu, Shangrong,Xu, Qiuneng,Liu, Li,Yan, Shenghu
p. 10004 - 10008
(2019/12/23)

The aminocarbonylation of 1,2-diiodoarenes with primary and secondary amines catalyzed by palladium complexes with imidazole ligands
The efficient carbonylative cyclization of 1,2-diiodobenzene with different primary and secondary amines was performed using a palladium complex with an imidazole ligand, PdCl2(BIM)2, as a catalyst. In reactions performed at 1 atm of CO with primary amines, phthalimides were obtained as the only products with yields of up to 100% in 4 h. An even shorter time, 1 h, was sufficient to obtain the same products employing methyl-2-iodobenzoate as a substrate instead of 1,2-diiodobenzene. In an analogous reaction with secondary amines, 1,2-diiodobenzene was converted to three products, formed in amounts dependent on the reaction conditions. The presence of Pd NPs and soluble palladium intermediates indicated their participation in the catalytic reaction.
Wójcik, Przemys?aw,Trzeciak, Anna M.
p. 73 - 83
(2018/05/22)

Imide arylation with aryl(TMP)iodonium tosylates
Herein, we describe the synthesis of N-aryl phthalimides by metal-free coupling of potassium phthalimide with unsymmetrical aryl(TMP)iodonium tosylate salts. The aryl transfer from the iodonium moiety occurs under electronic control with the electron-rich trimethoxyphenyl group acting as a competent dummy ligand. The yields of N-aryl phthalimides are moderate to high and the coupling reaction is compatible with electron-deficient and sterically encumbered aryl groups.
Basu, Souradeep,Sandtorv, Alexander H.,Stuart, David R.
supporting information
p. 1034 - 1038
(2020/05/06)

Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile
Herein we report a novel palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides with high atom- and step-economy. In our strategy, the imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available materials in a one-pot manner. Various phthalimide derivatives are constructed efficiently, including medicinally and biologically active phthalimide-containing compounds.
Ji, Fanghua,Li, Jianxiao,Li, Xianwei,Guo, Wei,Wu, Wanqing,Jiang, Huanfeng
p. 104 - 112
(2018/02/19)

L -Proline-Catalyzed Synthesis of Phthalimide Derivatives and Evaluation of Their Antioxidant, Anti-Inflammatory, and Lipoxygenase Inhibition Activities
A study was planned to synthesize the phthalimide derivatives as phthalimides have versatile biological activities. To synthesize the phthalimide derivatives, initially the reaction was optimized with various catalysts, and L-proline was found to be the best catalyst as it provided excellent yield. A series of phthalimide derivatives was synthesized by facile one-top reaction of phthalic acid with aryl amines under mild reaction conditions in the presence of L-proline as catalyst. Products were obtained in excellent yields and structurally characterized by 1H, 13C NMR, and mass spectral data. Products 1-7 were evaluated for antioxidant, anti-inflammatory, and lipoxygenase enzyme inhibition activities. Compounds 1 and 4 showed potent antioxidant activity under DPPH with IC50 values 27.3 and 25.0 μM when compared with the standard BHA (IC50 = 44.2 μM), respectively. Compounds 1 and 4 further showed strong lipoxygenase inhibition activity with IC50 values 21.34 and 20.45 μM when compared with standard baicalein (IC50 = 22.60 μM), respectively. Compound 2 was found to be promising and about equal to the used standard aspirin in the inhibition of bovine serum albumin denaturation, while other compounds showed weak-to-moderate % inhibition.
Perveen, Shagufta,Orfali, Raha
(2018/08/22)

Efficient copper-catalyzed N-arylation of NH-containing heterocycles and sulfonamides with arenediazonium tetrafluoroborates
A practical copper-catalyzed N-arylation of NH-containing heterocycles with arenediazonium tetrafluoroborates has been developed using CuCl as catalyst and K2CO3 as additive under ligand-free conditions. This reaction system has wide substrate scope including imides, 1H-pyrazole, 1H-tetrazoles, 1,2-benzisothiazol-3(2H)-one, and related sulfonamides and gives moderate to excellent yields (up to 95%) of the desired products. This strategy is very general, simple, environmentally friendly, and tolerant of oxygen.
Ouyang, Yu-Qing,Yang, Zhen-Hua,Chen, Zhong-Hui,Zhao, Sheng-Yin
supporting information
p. 771 - 778
(2017/04/06)

Palladium-Catalyzed Synthesis of 1H-Indenes and Phthalimides via Isocyanide Insertion
A new and versatile multicomponent domino strategy has been developed for the synthesis of a series of 1H-indene and phthalimide derivatives from simple and readily available starting materials. This process operating under mild conditions shows a broad substrate scope with moderate to excellent yields.
Wang, Xu,Xiong, Wenfang,Huang, Yubing,Zhu, Jiayi,Hu, Qiong,Wu, Wanqing,Jiang, Huanfeng
p. 5818 - 5821
(2017/11/10)

Thermolysis and radiofluorination of diaryliodonium salts derived from anilines
Aniline-derived diaryliodonium salts were synthesized and functionalized in good to excellent yields by judicious utilization of electron-withdrawing protecting groups. This simple approach opens another route to radiolabeling amino arenes in relatively complex molecules, such as flutemetamol.
Linstad, Ethan J.,Vāvere, Amy L.,Hu, Bao,Kempinger, Jayson J.,Snyder, Scott E.,DiMagno, Stephen G.
supporting information
p. 2246 - 2252
(2017/03/17)

An efficient synthesis of N-substituted phthalimides using SiO2-tpy-Nb as heterogeneous and reusable catalyst
A novel and efficient heterogeneous catalyst SiO2-tpy-Nb was developed, and its application in the preparation of N-substituted phthalimides from o-phthalic acids or anhydrides with amines provides the desired products in good to excellent yields. The catalyst was stable and recoverable for eight consecutive cycles without a significant loss in its activity. Furthermore, the catalyst is applicable in continuous flow which indicates its potential utilization in industrialization.
Wan, Li,Sun, Xiaoning,Shi, Songjie,Zhang, Jiawei,Li, Xin,Li, Zhenjiang,Guo, Kai
p. 30 - 34
(2016/09/28)

Synthetic method for N-substituted imide
The invention provides a synthetic method for N-substituted imide. According to the method, aromatic ketone and amine are used as substrates, air or oxygen is used as an oxygen source, and cyclic imide is produced under liquid phase conditions under the action of a catalyst. The method is mild in conditions, high in oxidation efficiency and high in product yield; and since the method uses air or oxygen as the oxygen source, the method is economic and environment-friendly and has good application prospect.
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Paragraph 0016; 0028; 0029; 0030; 0031

(2017/04/20)

Phthalimide-N-sulfonic acid, an efficient catalyst for the synthesis of various isoindoline-1,3-dione derivatives
An environmentally friendly method is described for the synthesis of various isoindoline-1,3-dione derivatives from the reaction of phthalic anhydride with aromatic/aliphatic amines in ethanol at 80 °C by phthalimide-N-sulfonic acid as an efficient heterogeneous acid catalyst. Some advantages include the metal-free and environmentally friendly protocol, simple operation and reusable processes, easy recovery, short reaction times, and high yields.
Habibi, Davood,Pordanjani, Hossein Mohammadkhani
p. 2293 - 2299
(2017/10/05)

A facile and practical copper diacetate mediated, ligand free C-N cross coupling of trivalent organobismuth compounds with amines and N-heteroarenes
In present work, an efficient Cu(OAc)2·H2O catalyzed protocol in the absence of any additional ligand has been developed for the N-arylation of amines and nitrogen containing heterocycles using trivalent organobismuth reagents under mild conditions. This protocol tolerates a variety of functional groups on amines and the organobismuth reagent with a high degree of chemoselectivity.
Jadhav,Pardeshi
p. 14531 - 14537
(2016/02/19)

Method for preparing 4-chlorine-2-(trifluoroacetyl) aniline hydrochloride hydrate
The invention discloses a method for preparing a 4-chlorine-2-(trifluoroacetyl) aniline hydrochloride hydrate, and belongs to the field of compound synthesis. P-chloroaniline serves as a raw material, the method includes the following steps that 1, the p-chloroaniline and acid anhydride are reacted to obtain 4-chlorine-N-phthaloyl aniline; 2, the 4-chlorine-N-phthaloyl aniline and trifluoroacetic acid ethyl ester are reacted under the effect of butyl lithium to obtain N-(4-chlorine-2 trifluoroacetyl phenyl)-phthalic diamide; 3, after the N-(4-chlorine-2 trifluoroacetyl phenyl)-phthalic diamide and hydrazine hydrate are heated and subjected to reflux in absolute ethyl alcohol, hydrochloric acid and glacial acetic acid are added, and the 4-chlorine-2-(trifluoroacetyl) aniline hydrochloride hydrate is obtained. The method is easy to operate, low in cost and suitable for industrial production, and the total yield is up to 82.2%.
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Paragraph 0019; 0020; 0024; 0025; 0029; 0030

(2016/11/21)

Direct Synthesis of Cyclic Imides from Carboxylic Anhydrides and Amines by Nb2O5 as a Water-Tolerant Lewis Acid Catalyst
In the 20 types of heterogeneous and homogenous catalysts screened, Nb2O5 showed the highest activity for the synthesis of N-phenylsuccinimide by dehydrative condensation of succinic anhydride and aniline. Nb2O5 was used in the direct imidation of a wide range of carboxylic anhydrides with NH3 or amines with various functional groups and could be reused. Kinetic studies showed that the Lewis acid Nb2O5 catalyst was more water tolerant than both the Lewis acidic oxide TiO2 and the homogeneous Lewis acid ZrCl4, which resulted in higher yields of imides through the use of Nb2O5. Int-imidation tactics: A general method for the direct synthesis of cyclic imides from cyclic anhydrides with amines (or ammonia) under solvent-free conditions is reported. Kinetic studies indicate that the Lewis acid sites of Nb2O5 are highly water tolerant, which results in high catalytic activity for imidation even in the presence of water formed during the reaction. The catalyst can be recovered and reused four times without a marked decrease in yield.
Ali, Md. A.,Moromi, Sondomoyee K.,Touchy, Abeda S.,Shimizu, Ken-Ichi
p. 891 - 894
(2016/03/15)

Cuprous Oxide Catalyzed Oxidative C-C Bond Cleavage for C-N Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines
Selective oxidative cleavage of a C-C bond offers a straightforward method to functionalize organic skeletons. Reported herein is the oxidative C-C bond cleavage of ketone for C-N bond formation over a cuprous oxide catalyst with molecular oxygen as the oxidant. A wide range of ketones and amines are converted into cyclic imides with moderate to excellent yields. In-depth studies show that both α-C-H and β-C-H bonds adjacent to the carbonyl groups are indispensable for the C-C bond cleavage. DFT calculations indicate the reaction is initiated with the oxidation of the α-C-H bond. Amines lower the activation energy of the C-C bond cleavage, and thus promote the reaction. New insight into the C-C bond cleavage mechanism is presented.
Wang, Min,Lu, Jianmin,Ma, Jiping,Zhang, Zhe,Wang, Feng
supporting information
p. 14061 - 14065
(2016/01/25)

Regioselective gold-catalyzed oxidative C-N bond formation
A novel protocol for the regioselective intermolecular amination of various arenes has been developed. By using an I(III) oxidant in the presence of a Au(I) catalyst, a direct and novel route for regioselectively accessing a variety of substituted aniline moieties has been achieved with yields as high as 90%. Mechanistic insight suggests that regioselectivity can be predicted based on electrophilic aromatic metalation patterns.
Marchetti, Louis,Kantak, Abhishek,Davis, Riley,Deboef, Brenton
supporting information
p. 358 - 361
(2015/01/30)

Nitrogen-centered radical-mediated C-H imidation of arenes and heteroarenes via visible light induced photocatalysis
The C-H imidation of arenes and heteroarenes has been achieved via visible light induced photocatalysis. In the presence of an iridium(iii) photoredox catalyst, the reaction of aromatic substrates with N-chlorophthalimide furnishes the N-aryl products at room temperature through a nitrogen-centered radical mediated aromatic substitution.
Kim, Hyejin,Kim, Taehoon,Lee, Dong Gil,Roh, Sang Weon,Lee, Chulbom
supporting information
p. 9273 - 9276
(2014/08/05)

An expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters
Phthalic, maleic and succinic anhydrides have been reacted with aromatic amines to obtain the corresponding monoacid monoamides. The latter have been each transformed into the corresponding cyclic imide derivatives by treating with SOCl2. Alternatively, anhydrides have been reacted with methanolic KOH to obtain monomethyl ester derivatives which on reaction with aromatic amines in the presence of EDC. HCl and HOBt give cyclic imide derivatives. Reaction of monoacid monoamides independently, with SOCl 2 at 0-5°C give the monoamide monoester derivatives. Treatment of monoamide monoester of malic anhydride with NaBH4 leads to the unusual reduction of C=C grouping as well as the carbonyl group of the ester group to from monoamide monoalcohol of succinic anhydride. Preparation of monoamide monoalcohol of succinic anhydride can also be achieved by chemoselective reduction of monoamide monoester of malic anhydride with Mg turnings yielding monoamide monoester of succinic anhydride followed by reduction of the latter with NaBH4.
Kumar, Padam Praveen,Reddy, Y. Dathu,Kumari, Y. Bharathi,Devi, B. Rama,Dubey
p. 392 - 398
(2014/05/06)

Open-air N-arylation of N-H heterocycles with arylboronic acids catalyzed by copper(II) Schiff base complexes
Two copper Schiff base complexes, in both homogeneous and heterogeneous forms, were prepared and characterized by using elemental analysis, FTIR, UV-Vis spectroscopy and scanning electron microscopy. The catalytic performances of these complexes were studied in the N-arylation of N-H heterocycles with arylboronic acids in methanol without any added base at 40 °C under open air. The effects of various parameters such as solvent and temperature on the reaction system were studied. The reaction is applicable to a wide variety of N-H heterocycles and arylboronic acids. The heterogeneous catalyst was recovered by simple filtration, and reusability experiments showed that this catalyst can be used five times without much loss in the catalytic activity.
Islam,Dey, Ram Chandra,Roy, Anupam Singha,Paul, Sumantra,Mondal, Sanchita
p. 961 - 969
(2015/01/09)

Aza-DielsAlder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)- ones via [4 + 2] imino-DielsAlder cyclization from N-aryl-3- hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3- hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl) vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.
Jha, Amitabh,Chou, Ting-Yi,ALJaroudi, Zainab,Ellis, Bobby D.,Cameron, T. Stanley
p. 848 - 857
(2014/05/06)

Magnetic nanocatalyst for the synthesis of maleimide and phthalimide derivatives
An efficient and green protocol for the synthesis of N-aryl maleimide and phthalimide derivatives has been developed. The high efficiency of the catalyst was observed due to the homogeneous distribution of the nanoparticles. The catalyst was fully characterised by physicochemical methods such as IR spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray diffraction, dynamic light scattering (DLS), energy dispersive X-ray spectrum and zeta potential measurement techniques. The ease of separation of the catalyst from the reaction mixture and its high activity are eco-friendly attributes of this system.
Thale, Pranila B.,Borase, Pravin N.,Shankarling, Ganapati S.
p. 59454 - 59461
(2015/02/19)

Synthesis and antiseizure evaluation of isoindoline-1,3-dione derivatives in mice
Epilepsy is the most common serious chronic noninfective neurological condition in the world. Despite the presence of various antiepileptic drugs in the market for epileptic patients, the necessity for development and discovery of novel antiepileptic drugs is felt. In fact, only 60-70 % of patients respond to the current drugs, and a high incidence of adverse effects is also observed. In the present study, a new series of phthalimide derivatives (compounds 3a-3m) were synthesized through the reaction of phthalic anhydride and various derivatives of aniline in toluene solvent (Reflux, 24 h). Antiepileptic activity of synthesized compounds (3a-3m) was investigated using two experimental models namely, maximal electroshock (MES) and pentylenetetrazole (PTZ), and the obtained results were compared with diazepam as reference drug. Neurotoxicity of compounds was also evaluated using rotarod model. Compound 3m with para methoxy substituent exhibited the anticonvulsant activity at 15.1 ± 1.53 (12.23-17.96) mg/kg dose in MES model compared to other derivatives. Unfortunately, none of the tested compounds rendered acceptable protection in subcutaneous PTZ model.
Aliabadi, Alireza,Gholamine, Babak,Karimi, Tahereh
p. 2736 - 2743
(2014/05/06)

Catalyst-free, eco-friendly, one-pot syntheses of 2-(3H-imidazo [4,5-b] pyridine-2-yl)-N-arylbenzamides in water
Eco-friendly, one-pot three-component syntheses of 2-(3H-imidazo [4,5-b]pyridine-2-yl)-N-arylbenzamides have been developed by combining phthalic anhydride with anilines and pyridine-2,3-diamine in water without any catalyst. These reactions involves easy workup, provide good yields and use of water as solvent which were the merits of this preparation.
Reddy, Y. Dathu,Kumar, P. Praveen,Devi, B. Rama,Reddy, Ch. Venkata Ramana,Dubey
p. 768 - 773
(2015/04/14)

Copper-catalyzed oxidation of arene-fused cyclic amines to cyclic imides
A novel copper-catalyzed oxidation of arene-fused cyclic amines to the corresponding cyclic imides has been developed. The reaction can be used to synthesize 1,3-disubstituted TPD in high yields.
Yan, Xiaoyu,Fang, Kun,Liu, Hailan,Xi, Chanjuan
supporting information
p. 10650 - 10652
(2013/11/06)

Studies on reactions of anhydrides with Schiff bases
Reaction of phthalic anhydride 1 with benzylidineanilines 2, in equimolar ratio in hot acetic acid, yields N-arylphthalimides 3. Compound 1 reacts with the arylimine part of the Schiff base eliminating benzaldehyde part 4 as the bye-product. This reaction of 1 with 2 is also found to occur with other anhydrides like succinic anhydride 5, maleic anhydride 7 and acetic anhydride 9 resulting in the formation of the corresponding N-arylimides, namely, succinicimide 6, maleicimide 8 and aceticimide 10 respectively. In all the above reactions, the by-product, i.e. benzaldehyde or p-chlorobenzaldehyde can be isolated and characterized as its 2,4-dinitrophenylhydrazone derivative. Probable mechanism for the formation of imides from the corresponding anhydrides and Schiff bases has been suggested.
Kumar, Padam Praveen,Mohiuddin,Rama Devi,Dubey
p. 686 - 690
(2013/07/11)

Imidazole-promoted synthesis of n-substituted phthalimide from N,N'-disubstituted ureas in solventless conditions
A series of N-substituted phthalimides was synthesized by a thermal reaction between N,N0-disubstituted ureas and phthalic acid catalyzed by imidazole in solventless conditions. The products have been obtained in moderate to good yields (53-92%). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
Neves Filho, Ricardo A. W.,Palm-Forster, Mieder A. T.,De Oliveira, Ronaldo N.
supporting information
p. 1571 - 1576
(2013/05/22)

A facile and green synthesis of N-substituted imides
Anhydrides 1, 6 and 10 have been reacted, independently, with aromatic primary amines 2 in solid phase by simple physical grinding of reactants with p-toluenesulphonicacid as a catalyst to yield corresponding open chain derivatives, monoacid monoamides3,7 and 11 respectively. The latter have each been transformed into the corresponding cyclic derivatives, i.e. imides 5, 9 and 13 respectively in solid phase by simple physical grinding of each with K 2CO3, alkylating agent and tetrabutylammoniumbromide as a catalyst with short reaction times. These cyclic imides can also be obtained by physical grinding of each of 3, 7 and 11 with dicyclohexylcarbodimide as a dehydrating agent in solid phase.
Kumar, Padam Praveen,Rama Devi,Dubey
p. 1166 - 1171
(2013/09/24)

Thermal and photochemical rearrangements of 3-arylamino-2-phenyl-1H-inden- 1-ones to n-arylphthal-imides
Upon heating to above their melting temperatures, 3-arylamino-2-phenyl-1H- inden-1-ones and 2,2′-diphenyl-3,3′-bis(arylimino)-[2,2′- biindan]-1,1′-dione undergo a skeletal rearrangement to afford N-arylphthalimides along with benzoic acid in the presence of atmospheric oxygen. The photoreaction of these compounds in acetonitrile also results in the formation of these products. The mechanism of the reactions, including the formation of a peroxyl radical followed by its conversion to a nitrogen-centered radical, is proposed.
Kawai, Masayuki,Sakanoshita, Eriko,Akita, Motoko,Kobayashi, Keiji
p. 1289 - 1299
(2013/07/19)

Sterically controlled, palladium-catalyzed intermolecular amination of arenes
We report the Pd-catalyzed amination of arenes to form N-aryl phthalimides with regioselectivity controlled predominantly by steric effects. Mono-, di-, and trisubstituted arenes lacking a directing group undergo amination reactions with moderate to high yields and high regioselectivities from sequential addition of PhI(OAc)2 as an oxidant in the presence of Pd(OAc) 2 as catalyst. This sterically derived selectivity contrasts that for analogous arene acetoxylation.
Shrestha, Ruja,Mukherjee, Paramita,Tan, Yichen,Litman, Zachary C.,Hartwig, John F.
supporting information
p. 8480 - 8483
(2013/07/19)

An efficient recyclable polymer supported copper(II) catalyst for C-N bond formation by N-arylation
Polymer supported Cu(II) catalyst was prepared, characterized and employed for the N-arylation and amination reaction of N-H heterocycles with aryl halides as well as arylboronic acids to afford the corresponding coupled products in good to excellent yields. This catalyst can be used several times with consistent catalytic activity.
Islam, Manirul,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Tuhina, Kazi,Mobarok, Manir,Paul, Sumantra,Salam, Noor,Hossain, Dildar
experimental part
p. 1171 - 1181
(2012/06/18)

Intermolecular oxidative C-N bond formation under metal-free conditions: Control of chemoselectivity between aryl sp2 and benzylic sp 3 C-H bond imidation
A new synthetic approach toward intermolecular oxidative C-N bond formation of arenes has been developed under transition-metal-free conditions. Complete control of chemoselectivity between aryl sp2 and benzylic sp 3 C-H bond imidation was achieved by the choice of nitrogen sources, representatively being phthalimide and dibenzenesulfonimide, respectively.
Kim, Hyun Jin,Kim, Jiyu,Cho, Seung Hwan,Chang, Sukbok
supporting information; experimental part
p. 16382 - 16385
(2011/12/13)

Polyethylene glycol as a nonionic liquid solvent for the synthesis of N-alkyl and N-arylimides
Polyethylene glycol (PEG) an inexpensive, nontoxic, environmentally friendly reaction medium for the synthesis of N-alkyl and N-arylphthalimides to afford the corresponding adducts in excellent yields under mild reaction conditions. The use of PEG avoids the use of acidic or basic catalysts, and moreover PEG could be recovered and reused.
Liang, Jun,Lv, Jing,Fan, Ji-Cai,Shang, Zhi-Cai
experimental part
p. 2822 - 2828
(2009/12/03)

An efficient protocol for the synthesis of N-Alkyl- and N-Arylimides using the lewis acidic ionic liquid choline chloride-2ZnCl2
Lewis acidic ionic liquid choline chloride-2ZnCl2 is shown to be for the first time an excellentmedium and efficient catalyst for the synthesis of N-alkyl- and N-arylimides in good yields under mild conditions.
Xiea, You-Teng,Houb, Rei-Sheu,Wangb, Huey-Min,Kangc, Iou-Jiun,Chena, Ling-Ching
experimental part
p. 839 - 842
(2010/08/13)

Efficient synthesis of aryl hydroxylactams by reducing imides with activated zinc dust
A series of aryl hydroxylactams (2a, 2b, 2d-2g, 2i-2k, 2m, and 2n) was synthesized by partially reducing aryl cyclic imides in moderate to excellent yields with activated zinc dust alone in acetic acid. This method was regiospecific and can be employed as an alternative for reported methods to partially reduce aryl cyclic imides. Copyright Taylor & Francis Group, LLC.
Yuan, Xiu-Hua,Zhang, Min-Jie,Kang, Chuan-Qing,Guo, Hai-Quan,Qiu, Xue-Peng,Gao, Lian-Xun
p. 435 - 444
(2007/10/03)

Nickel-catalyzed coupling of isocyanates with 1,3-iodoesters and halobenzenes: A novel method for the synthesis of imide and amide derivatives
Substituted imide and amide derivatives were conveniently prepared from the reaction of isocyanates with o-iodobenzoates and haloarenes catalyzed by the NiBr2(dppe)/dppe/Zn system in moderate to good yields with excellent tolerance of functional groups. The Royal Society of Chemistry 2005.
Hsieh, Jen-Chieh,Cheng, Chien-Hong
p. 4554 - 4556
(2007/10/03)

Organic reactions in ionic liquids: Ionic liquid-promoted efficient synthesis of N-alkyl and N-arylphthalimides
Phthalic anhydride reacts rapidly with Aromatic and aliphatic amines in ionic liquid [Bmim][PF6] or [Bmim][BF4] at 130°C to give N-aryl and N-alkylphthalimides in excellent yields.
Le, Zhang-Gao,Chen, Zhen-Chu,Hu, Yi,Zheng, Qin-Guo
p. 735 - 737
(2007/10/03)

A convenient procedure for the synthesis of phthalimides under microwave irradiation
An efficient, extremely fast and clean procedure for the synthesis of phthalimides 2 and 3 by the reaction of phthalic anhydrides 1 with urea and aromatic amines in the presence of catalytic amount of DMF under microwave irradiation is described. The products are obtained in quantitative yields and excellent purities.
Mogilaiah,Reddy, G. Randheer
p. 882 - 884
(2007/10/03)

Thalidomide analogues demonstrate dual inhibition of both angiogenesis and prostate cancer
The identification of agents with antiproliferative activity against endothelial cells has significant value for the treatment of many angiogenesis-dependent pathologies. Herein, we describe the discovery of a series of thalidomide analogues possessing inhibitory effects against both endothelial and prostate cancer cells. More specifically, several analogues exhibited low micromolar to mid-nanomolar potency in the inhibition of human microvascular endothelial cell (HMEC) proliferation, both in the presence and absence of vascular endothelial growth factor (VEGF), with the tetrafluorophthalimido class of compounds demonstrating the greatest potency. Additionally, all the compounds were screened against two different androgen independent prostate cancer cell lines (PC-3 and DU-145). Again, the tetrafluorophthalimido analogues exhibited the greatest effect with GI 50 values in the low micromolar range. Thalidomide was found to demonstrate selective inhibition of androgen receptor positive LNCaP prostate cancer cells. Furthermore, we showed that, as an example, tetrafluorophthalimido analogue 19 was able to completely inhibit the prostate specific antigen (PSA) secretion by the LNCaP cell line, while thalidomide demonstrated a 70% inhibition. We have also demonstrated that a correlation exists between HMEC and prostate cancer cell proliferation for this structural class. Altogether, our study suggests that these analogues may serve as promising leads for the development of agents that target both androgen dependent and independent prostate cancer and blood vessel growth.
Capitosti, Scott M.,Hansen, Todd P.,Brown, Milton L.
p. 327 - 336
(2007/10/03)

Synthesis and hypolipidemic activity of N-substituted phthalimides. Part V
A series of N-aryl- or N-(1,2,4-triazol-yl)-phthalimides (4a-4i) have been synthesized starting from phthalic anhydride (1) and an appropriate amine (2a-2i). All compounds presented hypolipidemic activity, but compound 4d proved to be the most active and reduced plasma cholesterol and triglyceride levels in Swiss white mice significantly.
Sena, Vera L.M.,Srivastava, Rajendra M.,Silva, Ricardo O.,Lima, Vera L.M.
p. 1283 - 1288
(2007/10/03)

A New Simple and Efficient Synthesis of N-Aryl Phthalimides in Ionic Liquid [bmim][PF6]
The room temperature ionic liquid [bmim][PF6], namely 1-butyl-3-methyl-imidazolium hexafluorophosphate, is used as an alternative solvent to classic solvents for the synthesis of a series of N-aryl phthalimides in good to excellent yields.
Zhou, Mei-Yun,Li, Yi-Qun,Xu, Xin-Ming
p. 3777 - 3780
(2007/10/03)

Protection of amino group as N-phthalyl derivative using microwave irradiation
The amino groups for various substrates are protected as N-phthalyl derivatives using solvent free neat condition under microwave exposure.
Khadilkar, Bhushan M.,Madyar, Virendra R.
p. 1083 - 1085
(2007/10/03)

Microwave-assisted parallel synthesis of a 2-aryl-1H-isoindole-1,3-dione library
An efficient parallel synthesis of a representative 28-member library of phthalimides is described. Parallel chromatography afforded the library members in suitable purity and with high yields.
Barchín, Bernardo M.,Cuadro, Ana M.,Alvarez-Builla, Julio
p. 343 - 345
(2007/10/03)