- Chemical and electrochemical reduction of the products from the reactions of isoindolines and tetracyanoethylene
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The reduction potentials of compounds resulting from the title reaction and containing one (4) or two (3) dicyanovinylidene moieties have been determined by means of cyclic voltammetry. Electrochemical reduction of the same compounds within the cavity of an EPR spectrometer led to the observation of radical species tentatively identified as the corresponding radical anions. EPR experiemnts have also provided indication that the first formed species in the butoxide reduction of 3 undergoes cleavage of the bond between the two heterocyclic systems evolving to radical anions identical to those obtained by similar reduction of compounds 4. Some models compounds have also been investigated for comparison purposes.
- Carloni,Carloni, Patricia,Greci,Greci, Lucedio,Stipa,Stipa, Pierluigi,Dopp,Doepp, Dietrich,El-Din Abdel Hafeez Hassan,Hassan, Alaa El-Din Abdel Hafeez,Alberti,Alberti, Angelo
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Read Online
- Effects of mixed aqueous-organic solvents on the rate of intramolecular carboxylic group-catalyzed cleavage of N-(4′-Methoxyphenyl -phthalamic acid
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Kinetic study on the cleavage of N-(4′-methoxyphenyl)phthalamic acid (NMPPAH) in mixed H2O-CH3CN and H2O-1,4-dioxan solvents containing 0.05 M HCI reveals the formation of phthalic anhydride (PAn)/phthalic acid (PA) as the sole or major product. Pseudo first-order rate constants (κ1) for the conversion of NMPPAH to PAn decrease nonlinearly from 60.4 × 10-5 to 2.64 × 10-5 s-1 with the increase in the contents of 1,4-dioxan from 10 to 80% v/v in mixed aqueous solvents. The rate of cleavage of NMPPAH in mixed H2O-CH3CN solvents at ≥50% v/v CH3CN follows an irreversible consecutive reaction path: NMPPAH →κ1 PAn →κ2 PA. The values of κ1 are larger in H2O-CH3CN than in H2O-1,4-dioxan solvents.
- Leng, Sim Yoke,Ariffin, Azhar,Niyaz Khan
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Read Online
- An Oxidation Study of Phthalimide-Derived Hydroxylactams
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A systematic study of the oxidation of 3-hydroxy-2-substituted isoindolin-1-ones (hy-droxylactams) and their conversion to the corresponding phthalimides was undertaken using three oxidants. Of special interest was the introduction of nickel peroxide (NiO2 ) as an oxidation system for hydroxylactams and comparison of its performance with the commonly used pyridinium chlorochromate (PCC) and iodoxybenzoic acid (IBX) reagents. Using a range of hydroxylactams, optimal conversions of these substrates to the corresponding imides was achieved with 50 equivalents of freshly prepared NiO2 in refluxing toluene over 5–32 h reaction times. By comparison, oxidations of the same substrates using PCC/silica gel (three equivalents) and IBX (three equivalents) required oxidation times of 1–3 h for full conversion but required lengthier purification. While nominal amounts (~25 mg) of substrate hydroxylactams were used to ascertain conversion, scale-up procedures using all three methods gave good to excellent isolated yields of imides.
- Adjei, Bernard L.,Luzzio, Frederick A.
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- “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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- Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes
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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
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supporting information
p. 2235 - 2239
(2020/03/13)
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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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- PPh3/I2/HCOOH: An efficient CO source for the synthesis of phthalimides
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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
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p. 1180 - 1185
(2019/01/26)
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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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- Phthalimide-N-sulfonic acid, an efficient catalyst for the synthesis of various isoindoline-1,3-dione derivatives
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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
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p. 2293 - 2299
(2017/10/05)
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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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- Palladium-Catalyzed Synthesis of 1H-Indenes and Phthalimides via Isocyanide Insertion
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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
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p. 5818 - 5821
(2017/11/10)
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- Efficient copper-catalyzed N-arylation of NH-containing heterocycles and sulfonamides with arenediazonium tetrafluoroborates
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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
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supporting information
p. 771 - 778
(2017/04/06)
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- INHIBITORS OF IRES-MEDIATED PROTEIN SYNTHESIS
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This disclosure relates to inhibitors of IRES-mediated protein synthesis, compositions comprising therapeutically effective amounts of these compounds, and methods of using those compounds and compositions in treating hyperproliferative disorders, e.g., cancers. This disclosure also relates to compositions comprising inhibitors of IRES-mediated protein synthesis and mTOR inhibitors, and to methods of treating cancer by conjoint administration of inhibitors of IRES-mediated protein synthesis and mTOR inhibitors.
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Page/Page column 38; 42
(2017/12/18)
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- Synthetic method for N-substituted imide
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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)
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- Stable and Reusable Binaphthyl-Supported Palladium Catalyst for Aminocarbonylation of Aryl Iodides
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A binaphthyl-supported Pd nanoparticles (Pd-BNP)-catalyzed aminocarbonylation of aryl iodides in the presence of carbon monoxide and amines for the synthesis of amides has been developed. This methodology provides an efficient route for the synthesis of a COX-2 enzyme inhibitor having anti-inflammatory activity.
- Sharma, Nidhi,Sekar, Govindasamy
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p. 314 - 320
(2016/02/14)
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- Facile synthesis of 3-substituted isoindolinones Dedicated to the memory of Professor Sharon Roscoe, a colleague and mentor instrumental in shaping the careers of many chemists
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The reactions of N-aryl-3-hydroxyisoindolinones and alkyl aryl ketones under Lewis acid-catalyzed anhydrous conditions afforded the corresponding substituted isoindolinones in good to excellent yields.
- Al-Jaroudi, Zainab,Mohapatra, Prabhu P.,Jha, Amitabh
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supporting information
p. 772 - 777
(2016/02/05)
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- A facile and practical copper diacetate mediated, ligand free C-N cross coupling of trivalent organobismuth compounds with amines and N-heteroarenes
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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
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p. 14531 - 14537
(2016/02/19)
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- Mechanochemical synthesis of phthalimides with crystal structures of intermediates and products
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A series of phthalimides have been successfully synthesized in the solid state by grinding (or kneading) of substituted phthalic anhydride and aniline derivatives. Selected products and intermediates were crystallized and characterized by crystallography leading to a potential rationale for the solid-state reactivity that suggests that co-crystals could serve as intermediates. This journal is
- Cola?o, Melwin,Dubois, Jean,Wouters, Johan
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p. 2523 - 2528
(2015/03/18)
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- Cuprous Oxide Catalyzed Oxidative C-C Bond Cleavage for C-N Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines
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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
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supporting information
p. 14061 - 14065
(2016/01/25)
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- Palladium-catalyzed cycloaminocarbonylation of 2-aminomethyl- and 2-alkylcarbamoylaryl tosylates with CO
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The palladium-catalyzed cycloaminocarbonylation of 2-(aminomethyl)aryl tosylates with CO has been established, by which a variety of salicylaldehyde derived 2-(aminomethyl)aryl tosylates may be cyclocarbonylated in the presence of CO, to afford the corresponding substituted isoindolinones in moderate to excellent yields. Furthermore, the method is also effective for the synthesis of isoindoline-1,3-diones and 2-alkyl-1H-benzo[e]isoindol-3(2H)-ones from 2-(N-alkylcarbamoyl)aryl tosylates and 1-(aminomethyl)naphthalene-2-yl tosylates, respectively.
- Liu, Bin,Wang, Yan,Liao, Benren,Zhang, Chunlei,Zhou, Xigeng
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supporting information
p. 5776 - 5780
(2015/09/29)
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- N -aminopyridinium salts as precursors for N-centered radicals - Direct amidation of arenes and heteroarenes
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Readily prepared N-aminopyridinium salts are valuable precursors for the generation of N-centered radicals. Reduction of these salts by single electron transfer allows for clean generation of amidyl radicals. It is shown that direct radical C-H amination of heteroarenes and arenes can be achieved with N-aminopyridinium salts under mild conditions by using photoredox catalysis.
- Greulich, Tobias W.,Daniliuc, Constantin G.,Studer, Armido
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supporting information
p. 254 - 257
(2015/03/05)
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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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- Regioselective gold-catalyzed oxidative C-N bond formation
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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
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supporting information
p. 358 - 361
(2015/01/30)
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- A phthalimidation protocol that follows protein defined parameters
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This work outlines the first phthalimidation protocol suitable for protein labeling and performed in aqueous media at room temperature and neutral pH with no catalyst or co-reagent required. The methodology is suitable for a range of amines and its efficiency was determined with chemoselective and site-selective protein labeling. This journal is
- Singudas, Rohith,Adusumalli, Srinivasa Rao,Joshi, Pralhad Namdev,Rai, Vishal
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supporting information
p. 473 - 476
(2015/01/09)
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- Nitrogen-centered radical-mediated C-H imidation of arenes and heteroarenes via visible light induced photocatalysis
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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
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supporting information
p. 9273 - 9276
(2014/08/05)
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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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- Magnetic nanocatalyst for the synthesis of maleimide and phthalimide derivatives
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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.
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p. 59454 - 59461
(2015/02/19)
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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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- An expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters
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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
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p. 392 - 398
(2014/05/06)
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- N-acyloxyphthalimides as nitrogen radical precursors in the visible light photocatalyzed room temperature C-H amination of arenes and heteroarenes
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This paper reports a room temperature visible light photocatalyzed method for the C-H amination of arenes and heteroarenes. A key enabling advance in this work is the design of N-acyloxyphthalimides as precursors to nitrogen-based radical intermediates for these transformations. A broad substrate scope is presented, including the selective meta-amination of pyridine derivatives. A radical aromatic substitution mechanism is proposed.
- Allen, Laura J.,Cabrera, Pablo J.,Lee, Melissa,Sanford, Melanie S.
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supporting information
p. 5607 - 5610
(2014/05/06)
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- Practical synthesis of phthalimides and benzamides by a multicomponent reaction involving arynes, isocyanides, and CO2/H2O
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Transition-metal-free multicomponent reactions involving arynes and isocyanides with either CO2 or H2O have been reported. With CO2 as the third component, the reactions resulted in the formation of N-substituted phthalimides. The utility of water as the third component furnished benzamide derivatives in moderate to good yields. These reactions took place under mild conditions with broad scope.
- Kaicharla, Trinadh,Thangaraj, Manikandan,Biju, Akkattu T.
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supporting information
p. 1728 - 1731
(2014/04/17)
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- Aza-DielsAlder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
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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
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p. 848 - 857
(2014/05/06)
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- Chitosan: An efficient recyclable catalyst for transamidation of carboxamides with amines under neat conditions
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A novel chitosan-catalyzed transamidation of carboxamides with amines under solvent-free conditions is described. A series of amide derivatives as well as more challenging aryl and alkyl amines with long-chain alkyl substituents could be selectively converted into the corresponding transamidation products, which are frequently found in biologically active compounds and pharmaceuticals. Under similar reaction conditions benzo[d]heterocycles were also obtained via a one-pot synthesis through transamidation and subsequent dehydration. Recyclability of chitosan was demonstrated, with quantitative yields of products obtained without any loss of catalytic activity. the Partner Organisations 2014.
- Nageswara Rao, Sadu,Chandra Mohan, Darapaneni,Adimurthy, Subbarayappa
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supporting information
p. 4122 - 4126
(2014/10/15)
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- Microwave-assisted heteropolyanion-based ionic liquids catalyzed transamidation of non-activated carboxamides with amines under solvent-free conditions
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An environmentally benign and highly efficient protocol for the transamidation of non-activated carboxamides with amines using heteropolyanion-based ionic liquids as catalysts under microwave-assisted and solvent-free conditions has been developed. As evaluated by the reactions of a structurally diverse set of amides and amines, the scope and utility of the transamidation proved to be quite general. Operational simplicity, solvent-free media, the potential reusability of catalysts and wide functional group tolerance are attractive features. This method provides a much improved protocol over the existing methods.
- Fu, Renzhong,Yang, Yang,Chen, Zhikai,Lai, Wenchen,Ma, Yongfeng,Wang, Quan,Yuan, Rongxin
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p. 9492 - 9499
(2015/03/04)
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- Palladium-catalyzed carbonylative synthesis of phthalimides from 1,2-dibromoarenes with molybdenum hexacarbonyl as carbon monoxide source
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We describe here a convenient and mild, carbon monoxide gas-free palladium-catalyzed procedure to obtain N-substituted phthalimides with molybdenum hexacarbonyl as carbon monoxide precursor. These conditions tolerate a number of functional groups on the benzene ring as well as a number of amines and give the corresponding phthalimides in good to excellent yields. Copyright
- Wu, Xiao-Feng,Oschatz, Stefan,Sharif, Muhammad,Flader, Anika,Krey, Lisa,Beller, Matthias,Langer, Peter
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supporting information
p. 3581 - 3585
(2014/01/06)
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- Synthesis and evaluation of some variants of the Nefkens' reagent
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A series of N-substituted phthalimides have been prepared in an effort to explore synthetic variants of the Nefkens' reagent. Three N-acylphthalimides [R = -CH3, -CH2CH3, and -C(CH3) 3] were prepared and employed for the protection of a series of representative amines. In addition, an N-methanesulfonylphthalimide and N-(diethylphosphoryl)phthalimide were also prepared. It was determined that among the phthalimides that were prepared N-propanoylphthalimide was the most effective reagent for the protection reaction.
- Goodman, Cassie A.,Hamaker, Christopher G.,Hitchcock, Shawn R.
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supporting information
p. 6012 - 6014
(2013/10/22)
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- A facile and green synthesis of N-substituted imides
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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
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p. 1166 - 1171
(2013/09/24)
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- Thermal and photochemical rearrangements of 3-arylamino-2-phenyl-1H-inden- 1-ones to n-arylphthal-imides
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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
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p. 1289 - 1299
(2013/07/19)
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- Sterically controlled, palladium-catalyzed intermolecular amination of arenes
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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.
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supporting information
p. 8480 - 8483
(2013/07/19)
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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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- L-Proline: An efficient catalyst for transamidation of carboxamides with amines
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In the presence of a catalytic amount of l-proline (10 mol %), transamidations of carboxamides with amines were achieved under solvent-free conditions. The transamidation process is compatible with a wide range of amines.
- Rao, Sadu Nageswara,Mohan, Darapaneni Chandra,Adimurthy, Subbarayappa
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supporting information
p. 1496 - 1499
(2013/06/27)
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- Carbonylative cyclization of o-halobenzoic acids for synthesis of N-substituted phthalimides using polymer-supported palladium-N-heterocyclic carbene as an efficient, heterogeneous, and reusable catalyst
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The carbonylative cyclization of o-iodobenzoic acid with a variety of primary amines and carbon monoxide (1 bar) using a polymer-supported palladium-N-heterocyclic carbene complex (PS-Pd-NHC) as the catalyst gives N-substituted 1H-isoindole-1,3(2H)-diones (phthalimides) in good to excellent yields with a short reaction time. The catalyst is efficient, heterogeneous, and phosphine-free, it exhibited remarkable activity and it is also recyclable (4 consecutive cycles). The use of methyl o-iodobenzoate as the substrate under these conditions also gave N-substituted 1H-isoindole-1,3(2H)-diones, but with lower yields. Cyclization of o-iodobenzyl alcohol with carbon monoxide under these conditions gave isobenzofuran-1(3H)-one (phthalide). Georg Thieme Verlag Stuttgart · New York.
- Khedkar, Mayur V.,Khan, Shoeb R.,Dhake, Kishor P.,Bhanage, Bhalchandra M.
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supporting information; experimental part
p. 2623 - 2629
(2012/09/05)
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- Boric acid: A highly efficient catalyst for transamidation of carboxamides with amines
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A novel method of transamidation of carboxamides with amines using catalytic amounts of readily available boric acid under solvent-free conditions has been developed. The scope of the methodology has been demonstrated with (i) primary, secondary, and tertiary amides and phthalimide and (ii) aliphatic, aromatic, cyclic, acyclic, primary, and secondary amines.
- Nguyen, Thanh Binh,Sorres, Jonathan,Tran, Minh Quan,Ermolenko, Ludmila,Al-Mourabit, Ali
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supporting information; experimental part
p. 3202 - 3205
(2012/08/07)
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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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- N -alkynyl imides (ynimides): Synthesis and use as a variant of highly labile ethynamine
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This study describes the first reliable synthesis of N-alkynyl imides (ynimides). This was accomplished with a copper-catalyzed coupling reaction between alkynyl(triaryl)bismuthonium salts and five-membered imides. We also found that it was possible to utilize N-ethynyl phthalimide as a variant of the highly labile ethynamine. 4-Amino-1,2,3-triazole was successfully obtained via the CuAAC reaction of N-ethynyl phthalimide with azide followed by hydrazinolysis of the phthaloyl protecting group.
- Sueda, Takuya,Oshima, Ayumi,Teno, Naoki
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supporting information; experimental part
p. 3996 - 3999
(2011/10/01)
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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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- Palladium-catalysed multicomponent aminocarbonylation of aryl or heteroaryl halides with Mo(CO)6i and aryl- or heteroarylamines using conventional heating
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Di(hetero)arylamides have been synthesized in short reaction times by palladium-catalysed multicomponent aminocarbonylation of either electron-deficient or electron-rich heteroaryl halides and p-iodoanisole with, several, arylamines bearing either electro
- Begouin, Agathe,Queiroz, Maria-Joao R. P.
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experimental part
p. 2820 - 2827
(2009/09/06)
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- Comparison of copper(II) acetate promoted N-arylation of 5,5-dimethyl hydantoin and other imides with triarylbismuthanes and aryl boronic acids
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This work demonstrates that the copper acetate promoted N-arylation of imides with boronic acids can be employed as a major method for the synthesis of N3-aryl hydantoins. Georg Thieme Verlag Stuttgart.
- Hügel, Helmut M.,Rix, Colin J.,Fleck, Karin
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p. 2290 - 2292
(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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