- π-Stacked hydrogen-bonded dimers in 2-(2-nitrophenylaminocarbonyl)-benzoic acid, and hydrogen-bonded sheets in orthorhombic and monoclinic polymorphs of 2-(4-nitrophenylaminocarbonyl)benzoic acid
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Molecules of 2-(2-nitrophenylaminocarbonyl)benzoic acid, C 14H10N2O5, are linked into centrosymmetric R22(8) dimers by a single O-H...O hydrogen bond [H...O = 1.78 A, O...O = 2.623 (2) A and O-H...O = 178°] and these dimers are linked into sheets by a single aromatic π-π stacking interaction. The isomeric compound 2-(4-nitrophenylamino-carbonyl)benzoic acid crystallizes in two polymorphic forms. In the orthorhombic form (space group P21212 1 with Z′ = 1, crystallized from ethanol), the molecules are linked into sheets of R44(22) rings by a combination of one N-H...O hydrogen bond [H...O = 1.96 A, N...O = 2.833 (3) A and N-H...O = 171°] and one O-H...O hydrogen bond [H...O = 1.78 A, O...O = 2.614 (3) A and O-H...O = 173°]. In the monoclinic form (space group P21/n with Z′ = 2, crystallized from acetone), the molecules are linked by a combination of two N-H...O hydrogen bonds [H...O = 2.09 and 2.16 A, N...O = 2.873 (4) and 2.902 (3) A, and N-H...O = 147 and 141°] and two O-H...O hydrogen bonds [H...O = 1.84 and 1.83 A, O...O = 2.664 (3) and 2.666 (3) A, and O-H...O = 166 and 174°] into sheets of some complexity. These sheets are linked into a three-dimensional framework by a single C-H...O hydrogen bond [H...O = 2.45 A, C...O = 3.355 (4) A and C-H...O = 160°].
- Glidewell, Christopher,Low, John N.,Skakle, Janet M.S.,Wardell, James L.
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Read Online
- “On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides
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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
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supporting information
p. 1738 - 1743
(2021/03/14)
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- Discovery of phthalimide derivatives as novel inhibitors of a soluble epoxide hydrolase
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Soluble epoxide hydrolase (sEH) inhibitors are effective in reducing blood pressure, inflammation, and pain in a number of mammalian disease models. As most classical urea-based sEH inhibitors suffer from poor solubility and pharmacokinetic properties, the development of novel sEH inhibitors with an improved pharmacokinetic specification has received a great deal of attention. In this study, a series of amide-based sEH inhibitors bearing a phthalimide ring as the novel secondary pharmacophore (P2) was designed, synthesized, and evaluated. Docking results illustrated that the amide group as the primary pharmacophore (P1) was placed at a suitable distance from the three key amino acids (Tyr383, Tyr466, and Asp335) for an effective hydrogen bonding. In agreement with these findings, most of the newly synthesized compounds demonstrated moderate?to?high sEH inhibitory activities, relative to 12-(3-adamantan-1-yl-ureido)dodecanoic acid as the reference standard. Compound 12e with a 4-methoxybenzoyl substituent exhibited the highest sEH inhibitory activity, with an IC50 value of 1.06 nM. Moreover, the ADME properties of the compounds were evaluated in silico, and the results revealed appropriate predictions.
- Mahlooji, Iman,Shokri, Maryam,Manoochehri, Rana,Mahboubi-Rabbani, Mohammad,Rezaee, Elham,Tabatabai, Sayyed Abbas
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- Palladium Catalyzed Regioselective Synthesis of Substituted Biaryl Amides through Decarbonylative Arylation of Phthalimides
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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
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p. 3968 - 3976
(2019/03/26)
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- Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides
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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
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p. 1898 - 1907
(2019/02/05)
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- Imide arylation with aryl(TMP)iodonium tosylates
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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.
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supporting information
p. 1034 - 1038
(2020/05/06)
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- The aminocarbonylation of 1,2-diiodoarenes with primary and secondary amines catalyzed by palladium complexes with imidazole ligands
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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.
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- L -Proline-Catalyzed Synthesis of Phthalimide Derivatives and Evaluation of Their Antioxidant, Anti-Inflammatory, and Lipoxygenase Inhibition Activities
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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
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- Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives
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The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.
- Yuan, Yu-Chao,Kamaraj, Raghu,Bruneau, Christian,Labasque, Thierry,Roisnel, Thierry,Gramage-Doria, Rafael
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supporting information
p. 6404 - 6407
(2017/12/08)
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- Thalidomide analogues: Tumor necrosis factor-alpha inhibitors and their evaluation as anti-inflammatory agents
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A series of related thalidomide derivatives (2-9) were synthesized by microwave irradiation and evaluated for anti-inflammatory activity. Such activity was assessed in vivo and ex vivo. Compounds 2, 8 and 9 showed the highest levels of inhibition of TNF-α production. On rat paw edema and hyperalgesia assays, compound 9, (1,4-phthalazinedione) demonstrated the highest in vivo anti-inflammatory activity. Thus, compound 9 can be considered as a promising compound to be subjected to further modification to obtain new agents for the treatment of inflammatory diseases.
- Casal, Juan José,Bollini, Mariela,Lombardo, María Elisa,Bruno, Ana María
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p. 114 - 119
(2016/01/09)
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- Carbonylative synthesis of phthalimides and benzoxazinones by using phenyl formate as a carbon monoxide source
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A simple and efficient palladium-catalyzed carbonylative cyclization of N-substituted 2-iodobenzamides and 2-iodoanilides was investigated for the synthesis of phthalimides and benzoxazinones, respectively, by using phenyl formate as a CO source. The present catalytic protocol circumvents the use of an expensive phosphine ligand as well as solvent in the case of the phthalimide synthesis. Moreover, mild reaction conditions and a tolerance of various functional groups enhance the general applicability of this method.
- Chavan, Sujit P.,Bhanage, Bhalchandra M.
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p. 2405 - 2410
(2015/04/22)
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- Synthesis and antiseizure evaluation of isoindoline-1,3-dione derivatives in mice
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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
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p. 2736 - 2743
(2014/05/06)
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- Catalyst-free, eco-friendly, one-pot syntheses of 2-(3H-imidazo [4,5-b] pyridine-2-yl)-N-arylbenzamides in water
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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
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p. 768 - 773
(2015/04/14)
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- Imidazole-promoted synthesis of n-substituted phthalimide from N,N'-disubstituted ureas in solventless conditions
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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.
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supporting information
p. 1571 - 1576
(2013/05/22)
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- Efficient synthesis of 2-substituted phthalimides from phthalic acids in one step
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Efficient procedures for synthesizing 2-substituted phthalimide (isoindole-1,3-dione) analogues starting from phthalic acids have been developed by using experimental design. The phthalimide central fragment frequently appears in biologically active compounds, materials, catalysts, and fluorescent probes, and therefore the development of general, fast, and convenient synthetic methods to this scaffold under neutral, acidic, and basic conditions would be attractive. After an initial screening, the use of acetonitrile, acetic acid, or pyridine in combination with microwave heating proved most promising. Experimental design was applied to these conditions to optimize the time, temperature, and concentration. This strategy has successfully generated synthetic methods that have been used to synthesize a series of phthalimides from phthalic acids and various amines or anilines in excellent yields. The developed methods have proven to be general, fast, convenient, and economic, and thus are expected to have broad utility to efficiently construct novel compounds for future biological and chemical applications. Efficient procedures for synthesizing 2-substituted phthalimide (isoindole-1,3-dione) analogues starting from phthalic acids have been developed by using experimental design. The developed methods are fast, general, high-yielding, do not use additives, and are based on 1:1 molar ratios.
- Chorell, Erik,Chorell, Elin
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supporting information
p. 7512 - 7516
(2013/12/04)
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- Docking, synthesis, and pharmacological evaluation of isoindoline derivatives as anticonvulsant agents
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Eleven analogs of N-arylisoindoline pharmacophore were synthesized and evaluated for their anticonvulsant activities. The in vivo screening data acquired indicate that all the analogs have the ability to protect against pentylenetetrazole-induced seizure. Compounds 2, 6, and 11 elevated clonic seizure thresholds at 30 min which were more active than reference drug phenytoin, and compounds 2, 7, and 11 showed marked anticonvulsant activity on tonic seizure. The most potent compounds were 2 and 11 which had comparative activity to the phenytoin. Using a model of the open pore of the Na channel, we have docked all compounds. Docking studies have revealed that these compounds interacted mainly with residues II-S6 of NaV1.2 by making hydrogen bonds and have additional hydrophobic interactions with other domains in the channel's inner pore.
- Davood, Asghar,Amini, Mohsen,Azimidoost, Leila,Rahmatpour, Somaieh,Nikbakht, Ali,Iman, Maryam,Shafaroodi, Hamed,Ansari, Abdollah
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p. 3177 - 3184
(2013/07/19)
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- Palladium on carbon: An efficient, heterogeneous and reusable catalytic system for carbonylative synthesis of N-substituted phthalimides
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The application of palladium on carbon (Pd/C) as a heterogeneous recyclable catalyst was investigated for the double carbonylation of o-dihaloarenes with amines providing excellent yield of N-substituted phthalimides in shorter reaction time as compared to earlier reported homogeneous protocols. Furthermore, the scope of the developed protocol was applied for the synthesis N-substituted phthalimides from o-halobenzoates and o-halobenzoic acid via a single step carbonylative cyclization reaction. The developed methodology describes an efficient one-step approach for the synthesis of an important class of heterocycles and tolerates a wide variety of functional groups. It circumvents the use of phosphine ligands with an additional advantage of catalyst recyclability for up to eight consecutive cycles. Copyright
- Khedkar, Mayur V.,Khan, Shoeb R.,Sawant, Dinesh N.,Bagal, Dattatraya B.,Bhanage, Bhalchandra M.
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supporting information; experimental part
p. 3415 - 3422
(2012/02/05)
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- PHTHALIMIDE DERIVATIVE METABOTROPIC GLUTAMATE R4 LIGANDS
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Disclosed are mGluR4 positive allosteric modulator ligands of general formula (I) and radiolabeled derivates, their use as therapeutic agents for the treatment of central nervous system disorders modulated by mGluR4 and as ligands for the labeling and diagnostic imaging of mGluR4 in mammals.
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Page/Page column 26-27
(2010/04/25)
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- Polyethylene glycol as a nonionic liquid solvent for the synthesis of N-alkyl and N-arylimides
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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
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experimental part
p. 2822 - 2828
(2009/12/03)
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- An efficient protocol for the synthesis of N-Alkyl- and N-Arylimides using the lewis acidic ionic liquid choline chloride-2ZnCl2
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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
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experimental part
p. 839 - 842
(2010/08/13)
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- The kinetic study on the effects of mixed aqueous-organic solvents on the rate of O- And N- cyclisation of N-(4′-nitrophenyl)phthalamic acid
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The pseudo-first-order rate constants (kobs) for the intramolecular carboxylic group-assisted cleavage of N-(4′-nitrophenyl) phthalamic acid (1) show nonlinear decrease of - 17-fold and - 117-fold with the increase in the respective contents Of CH3CN (10-80% v/v) and 1,4-dioxan (9.5-79.4% v/v) in mixed aqueous solvents. The fraction of Ncyclization of 1 leading to the formation of N-(4′-nitrophenyl) phthalimide, 2, remains almost zero at ≤40% v/v CH3CN while it increases from 0.06 to 0.49 with increase in CH3CN content (50-80% v/v) at 1.0x10-3 M HCl. However, the observed data reveal an almost absence of N-cyclization within 1,4-dioxan content range 10-80% v/v.
- Ahmad, Wan Hamdah Wan,Ariffin, Azhar,Khan, M. Niyaz
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p. 416 - 421
(2008/02/09)
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- Nickel-catalyzed coupling of isocyanates with 1,3-iodoesters and halobenzenes: A novel method for the synthesis of imide and amide derivatives
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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
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p. 4554 - 4556
(2007/10/03)
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- Organic reactions in ionic liquids: Ionic liquid-promoted efficient synthesis of N-alkyl and N-arylphthalimides
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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
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p. 735 - 737
(2007/10/03)
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- A convenient procedure for the synthesis of phthalimides under microwave irradiation
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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
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p. 882 - 884
(2007/10/03)
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- A New Simple and Efficient Synthesis of N-Aryl Phthalimides in Ionic Liquid [bmim][PF6]
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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
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p. 3777 - 3780
(2007/10/03)
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- A rapid synthesis of N-aryl phthalimides under microwave irradiation in the absence of solvent
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A mixture of phthalic anhydride (1) and aromatic amines (2a-h) were irradiated in a microwave oven for 2-10 min to provide N-aryl phthalimides (3a-h) in 91-95% yields.
- Li, Hui-Zhang,Zhang, Jin-Song,Zhou, Ya-Ming,Li, Tong-Shuang
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p. 927 - 930
(2007/10/03)
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- The cyclisation of substituted phthalanilic acids in acetic acid solution. A kinetic study of substituted N-phenylphthalimide formation
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One novel and ten known substituted 3′- and 4′-phthalanilic acids have been prepared. These have been cyclised to two novel and nine known substituted N-phenylphthalimides by heating with glacial acetic acid. Both phthalanilic acids and imides have been characterised in detail and spectroscopic data are given. The kinetics of cyclisation for phthalanilic acids has been examined in detail, and it has emerged that a complex mechanism is operating. This initially involves a reversible, solvent assisted intramolecular nucleophilic attack by amide nitrogen on the carboxylic acid carbonyl. Clear evidence is seen for a long-lived intermediate as a precursor to imide formation. The observed kinetics are rationalised using a model of rapid pre-equilibration, followed by the slow breakdown of the intermediate to imide. Observed rate constants for pre-equilibration show a well behaved, linear Hammett plot (ρ = -1.1), whereas those for formation of imide do not.
- Perry, Christopher J.,Parveen, Zahida
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p. 512 - 521
(2007/10/03)
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- Synthesis and anticonvulsant and neurotoxic properties of substituted N- phenyl derivatives of the phthalimide pharmacophore
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A series of compounds including 4-amino (1), 3-amino (2), 4-nitro (3), 2-methyl-3-amino (4), 2-methyl-3-nitro (5), 2-methyl-4-amino (6), 2-methyl-4- nitro (7), 2-methyl-5-amino (8), 2-methyl-5-nitro (9), 2-methyl-6-amino (10), 2-methyl-6-mitro (11), 2,6-dimethyl (12), 2-methyl-3-carboxy (13), 2- methoxycarbonyl (14), 2-methyl-4-methoxy (15), 2,4-dimethoxy (16), 2-chloro- 4-amino (17), and 2-chloro-4-nitro (18) N-phenyl substituents of phthalimide were evaluated along with N-[3-methyl-(2-pyridinyl)]phthalimide (19), N-(3- amino-2-methylphenyl)succinimide (20), and phenytoin for anticonvulsant and neurotoxic properties. Initial screening in the intraperitoneal (ip) maximal electroshock-induced seizure (MES) test and the subcutaneous pentylenetetrazol-induced seizure (scPtz) test in mice led to the selection of 1, 2, 4, 10, 12, 17, and 19 for oral MES evaluation in rats. The resultant ED50 values for 4, 10, 17, and phenytoin were 8.0, 28.3, 5.7 and 29.8 mg/kg, respectively. In the batrachotoxin affinity assay, IC50 values for 17 and phenytoin were 0.15 and 0.93 μM, respectively, and in the recently validated magnesium deficiency-dependent audiogenic seizure test, ED50 values of 5.2 and 23 mg/kg were obtained for 17 and phenytoin, respectively. Electrophysiology studies on compound 17 point out its ability to (i) potentiate GABA-evoked current responses with a failure to directly activate the GABAA receptor and (ii) to affect, at 100 μM excitatory non NMDA, but not NMDA, receptors with a 25% block of kainate-evoked response. Electrophysiology measurements on voltagegated sodium channels in N1E-115 neuroblastoma cells confirm voltage-dependent block of these channels by compound 17. In view of its interaction with multiple ion channels, one would predict that compound 17 might be active in a wide range of seizure models.
- Vamecq, Joseph,Bac, Pierre,Herrenknecht, Christine,Maurois, Pierre,Delcourt, Philippe,Stables, James P.
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p. 1311 - 1319
(2007/10/03)
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- Multivariate regression with substituent shift increments. IV. 2-(4-X-phenyl)-1,3-dihydro-2H-isoindole-1,3-diones and 3-(4-X-phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones
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Two series of para disubstituted benzenes were studied: 2-(4-X-phenyl)-1,3-dihydro-2H-isoindole-1,3-diones (1) and 3-(4-X-phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones (2). Their 1H and 13C chemical shifts were correlated with substituent shift increments (SSI) aj and zj, respectively. For 13C chemical shifts, all four zj values, zj, zo, zm, and zp, were used to check the assignment and to find out possible variables for improvement of regression equations. Significant deviations from plain additivity were observed in the case of δH3 and δC3 chemical shifts. This can be explained by changes in diamagnetic anisotropy contribution induced by different twist of 4-substituent from the benzene plane caused by variable substituent in position 1.
- Holik, Miroslav,Friedl, Zdenek,Waisser, Karel,Gregor, Jiri
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p. 1709 - 1726
(2007/10/03)
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- Microwave Irradiation Promoted Reactions of Anhydrides with Isocyanates. Preparation of N-Substituted Phthalimides
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The synthesis of N-substituted phthalimides by the condensation of anhydrides and isocyanates was conducted efficiently in a few minutes in unmodified commercial microwave ovens using unsealed vessels.
- Khajavi, Mohammad S.,Nikpour, Farzad,Hajihadi, Mostafa
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- Studies on the Mode of Ring-Opening of N-aryl Phthalisoimidium Perchlorates
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N-Arylphthalisoimidium perchlorates (1a, b and 7) react with primary amines via ring-opening to give N,N'-disubstituted phthalamides (3a-c and 9a,b) respectively. (1a reacts with aromatic hydrocarbons under Friedel-Crafts conditions to give 2,3-diaryl-3-hydroxyphthalimidines (11a-c) while (1b) undergoes rearrangement to (12) via the intermediate formation of the isoimide (13) under the same reaction conditions. Key words: isoimidium salts, phthalamides, hydroxyphthalimidines
- Ismail, M. Fekry,Sayed, F. S.,Derbala, H. A. Y.,Mansour, M. M.
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p. 1114 - 1119
(2007/10/02)
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- TRANSMISSION OF SUBSTITUENT EFFECTS IN N-(p-SUBSTITUTED PHENYL)-PHTHALIMIDES
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Chemical shifts of benzene part of the title compounds have been correlated with substituent chemical shift (SCS) increments a for 1H and z for 13C NMR spectra.These correlations gave pieces of information not only about the through-conjugation of substituents but also about the change of the twist about the central N-C bond with the change of substituent in the para-position.In such a way the electronic effects of substituents have been studied together with the effects due to conformational changes which manifest themselves with the change in the van der Waalsrepulsion and/or diamagnetic anisotropy of double bond.Chemical shifts in phthalimide part of molecule have been related to the electronic effect of distant substituent after separation of the main source of variation from random error by principal component analysis.
- Holik, Miroslav,Matejkova, Bozena
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p. 261 - 272
(2007/10/02)
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- Carboxamide Participation in the Hydrolysis of p'-Substituted Phthalanilic Acids
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The hydrolysis rate constants of p'-substituted phthalanilic acids have been determined in 40percent aq. dioxane (v/v) at pH 8.0.The acids with electron-donating p'-substituents hydrolyze faster than those with electron-withdrawing p'-substituents.The product of hydrolysis has been isolated and identified to be the corresponding substituted imide.The Hammett plot is linear and a probable mechanism for the hydrolysis has been proposed.
- Bansal, R. K.,Jain, S. K.
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p. 785 - 786
(2007/10/02)
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