- N-PHENYLISONAPHTALIMIDE. STRUCTURE OF THE PRODUCT OF THE REACTION OF 1,8-NAPHTALOYL CHLORIDE WITH ANILINE.
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It is shown that N-phenylisonaphtalimide rather than N-phenylnaphtalimide, as previously assumed, is formed in the reaction of 1,8-naphtaloyl chloride with aniline.
- Ganin, E. V.,Makarov, V. F.,Nikitin, V. I.
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- N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides
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A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.
- Manoj Kumar, Mesram,Venkataramana, Parikibanda,Yadagiri Swamy, Parikibanda,Chityala, Yadaiah
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supporting information
p. 17713 - 17721
(2021/11/10)
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- Electro-mediated PhotoRedox Catalysis for Selective C(sp3)–O Cleavages of Phosphinated Alcohols to Carbanions
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We report a novel example of electro-mediated photoredox catalysis (e-PRC) in the reductive cleavage of C(sp3)?O bonds of phosphinated alcohols to alkyl carbanions. As well as deoxygenations, olefinations are reported which are E-selective and can be made Z-selective in a tandem reduction/photosensitization process where both steps are photoelectrochemically promoted. Spectroscopy, computation, and catalyst structural variations reveal that our new naphthalene monoimide-type catalyst allows for an intimate dispersive precomplexation of its radical anion form with the phosphinate substrate, facilitating a reactivity-determining C(sp3)?O cleavage. Surprisingly and in contrast to previously reported photoexcited radical anion chemistries, our conditions tolerate aryl chlorides/bromides and do not give rise to Birch-type reductions.
- Barham, Joshua P.,K?nig, Burkhard,Karl, Tobias A.,Reiter, Sebastian,Tian, Xianhai,Yakubov, Shahboz,de Vivie-Riedle, Regina
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supporting information
p. 20817 - 20825
(2021/08/18)
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- Modelling and Phenotypic Screening of NAP-6 and 10-Cl-BBQ, AhR Ligands Displaying Selective Breast Cancer Cytotoxicity in Vitro
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To exploit the interaction of the aryl hydrocarbon receptor (AhR) pathway in developing breast-cancer-specific cytotoxic compounds, we examined the breast cancer selectivity and the docking pose of the AhR ligands (Z)-2-(2-aminophenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (NAP-6; 5) and 10-chloro-7H-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one (10-Cl-BBQ; 6). While the breast cancer selectivity of 5 in vitro is known, we discuss the SAR around this lead and, by using phenotypic cell-line screening and the MTT assay, show for the first time that 6 also presents with breast cancer selectivity, notably in the triple-negative (TN) receptor breast cancer cell line MDA-MB-468, the ER+ breast cancer cell lines T47D, ZR-75-1 and the HER2+ breast cancer cell line SKBR3 (GI50 values of 0.098, 0.97, 0.13 and 0.21 μM, respectively). Indeed, 6 is 55 times more potent in MDA-MB-468 cells than normal MCF10A breast cells (GI50 of 0.098 vs 5.4 μM) and more than 130 times more potent than in cell lines derived from pancreas, brain and prostate (GI50 of 0.098 vs 10–13 μM). Molecular docking poses of 5 and 6 together with analogue synthesis and phenotypic screening show the importance of the naphthalene moiety, and an ortho-disposed substituent on the N-phenyl moiety for biological activity.
- Baker, Jennifer R.,Pollard, Brett L.,Lin, Andrew J. S.,Gilbert, Jayne,Paula, Stefan,Zhu, Xiao,Sakoff, Jennette A.,McCluskey, Adam
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p. 1499 - 1512
(2021/03/03)
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- Synthesis, spectroscopic and structural characterization and solution stability of ruthenium sandwich complexes containing 1,8-naphthalimide ligands
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Two different N-substituted naphthalimide ligands 1 (bearing a phenyl on the imide nitrogen) and 2 (bearing a benzyl on the imide nitrogen) have been synthesized and reacted with the cationic organometallic fragment [Cp*Ru(ACN)3]PF6. Ligand 1 brings to the formation of a sandwich complex (3Naph) where Ru is positioned on the naphthalene platform, while the N-imide phenyl substituent is not involved in coordination. This has been proven by single-crystal X-ray diffraction analysis conducted on crystals of 3Naph, revealing the first sandwich complex structurally characterized containing a naphthaleneimide ligand η6-coordinated to a metal. Ligand 2 shows instead a different behavior, leading to the formation of two isomeric complexes (4Naph and 4Bz), where Ru is placed on the naphthalene platform and on the N-imide benzyl substituent, in a rough 1:1 ratio. Complex 3Naph results very labile in coordinating solvents, such as acetonitrile, where it undergoes a fast and quantitative ligand solvolysis, with formation of free 1 and [Cp*Ru(ACN)3]PF6. In the cases of complexes 4, only complex 4Naph undergoes a fast and quantitative ligand solvolysis once dissolved in acetonitrile, whereas complex 4Bz results more stable.
- Pioli, Marianna,Loffi, Cecilia,Mazzeo, Paolo Pio,Bacchi, Alessia,Pelagatti, Paolo
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supporting information
(2021/01/07)
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- One-Pot Domino Carbonylation Protocol for Aromatic Diimides toward n-Type Organic Semiconductors
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Aromatic diimides are one of the most important chromophores in the construction of n-type organic semiconductors, which lag far behind their p-type counterpart but are necessary for ambipolar transistors, p-n junctions and organic complementary circuits. Herein, we establish a facile one-pot domino synthetic protocol for aromatic diimides via palladium-catalyzed carbonylation of tetrabromo aromatic precursors. Taking tetrabromocorannulene (TBrCor) and tetrabromo-2,7-di-tert-butylpyrene (TBrPy) as the typical examples, we obtained diimide derivatives in yields of about 50 percent, one order of magnitude higher than that of the traditional multi-step diimidization. As demonstrated in the case of corannulene diimide, the efficient diimidization not only allows the LUMO levels to be lowered significantly but also provides an ordered and closer packing structures, opening up possibilities to the development of n-type semiconducting materials based on a variety of aromatic systems.
- Dong, Huanli,Fu, Xiaolong,Hu, Wenping,Li, Yang,Ni, Zhenjie,Siegel, Jay S.,Zhen, Yonggang
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supporting information
p. 14024 - 14028
(2020/06/17)
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- Cu-catalyzed N-3-Arylation of Hydantoins Using Diaryliodonium Salts
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A general Cu-catalyzed, regioselective method for the N-3-arylation of hydantoins is described. The protocol utilizes aryl(trimethoxyphenyl)iodonium tosylate as the arylating agent in the presence of triethylamine and a catalytic amount of a simple Cu-salt. The method is compatible with structurally diverse hydantoins and operates well with neutral aryl groups or aryl groups bearing weakly donating/withdrawing elements. It is also applicable for the rapid diversification of pharmaceutically relevant hydantoins.
- Neerbye Berntsen, Linn,Nova, Ainara,Wragg, David S.,Sandtorv, Alexander H.
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p. 2687 - 2691
(2020/04/10)
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- Persistent Room-Temperature Radicals from Anionic Naphthalimides: Spin Pairing and Supramolecular Chemistry
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N-Substituted naphthalimides (NNIs) have been shown to exhibit highly efficient and persistent room-temperature phosphorescence from an NNI-localized triplet excited state, when the N-substitution is a sufficiently strong donor and mediates an intramolecu
- Huang, Wenhuan,Chen, Biao,Zhang, Guoqing
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supporting information
p. 12497 - 12501
(2019/09/10)
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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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- Target Enzyme-Activated Two-Photon Fluorescent Probes: A Case Study of CYP3A4 Using a Two-Dimensional Design Strategy
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The rapid development of fluorescent probes for monitoring target enzymes is still a great challenge owing to the lack of efficient ways to optimize a specific fluorophore. Herein, a practical two-dimensional strategy was designed for the development of an isoform-specific probe for CYP3A4, a key cytochrome P450 isoform responsible for the oxidation of most clinical drugs. In first dimension of the design strategy, a potential two-photon fluorescent substrate (NN) for CYP3A4 was effectively selected using ensemble-based virtual screening. In the second dimension, various substituent groups were introduced into NN to optimize the isoform-selectivity and reactivity. Finally, with ideal selectivity and sensitivity, NEN was successfully applied to the real-time detection of CYP3A4 in living cells and zebrafish. These findings suggested that our strategy is practical for developing an isoform-specific probe for a target enzyme.
- Ning, Jing,Wang, Wei,Ge, Guangbo,Chu, Peng,Long, Feida,Yang, Yongliang,Peng, Yulin,Feng, Lei,Ma, Xiaochi,James, Tony D.
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supporting information
p. 9959 - 9963
(2019/06/24)
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- Aggregation-induced emission, multiple chromisms and self-organization of N-substituted-1,8-naphthalimides
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Most aggregation-induced emission (AIE) luminogens possess propeller-like aromatic stator-rotor structures, such as silole, tetraphenylethylene (TPE) and triphenylamine (TPA), to restrict intra-molecular motions (RIM) and avoid aggregation-caused quenchin
- Ge, Shusheng,Li, Baoyan,Meng, Xinlei,Yan, Han,Yang, Mei,Dong, Ben,Lu, Yun
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p. 147 - 153
(2017/09/15)
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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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- Versatile Room-Temperature-Phosphorescent Materials Prepared from N-Substituted Naphthalimides: Emission Enhancement and Chemical Conjugation
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Purely organic materials with room-temperature phosphorescence (RTP) are currently under intense investigation because of their potential applications in sensing, imaging, and displaying. Inspired by certain organometallic systems, where ligand-localized
- Chen, Xiaofeng,Xu, Cheng,Wang, Tao,Zhou, Cao,Du, Jiajun,Wang, Zhongping,Xu, Hangxun,Xie, Tongqing,Bi, Guoqiang,Jiang, Jun,Zhang, Xuepeng,Demas, James N.,Trindle, Carl O.,Luo, Yi,Zhang, Guoqing
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supporting information
p. 9872 - 9876
(2016/08/16)
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- METHODS AND COMPOSITIONS FOR TREATING BETA-THALASSEMIA AND SICKLE CELL DISEASE
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Compounds, pharmaceutical compositions, and methods for treating anemia β-thalassemia anemia or sickle cell anemia.
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Paragraph 0221; 0222
(2016/05/19)
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- Methods and compositions for treating beta-thalassemia and sickle cell disease
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Compounds, pharmaceutical compositions, and methods for treating anemia beta-thalassemia anemia or sickle cell anemia are disclosed.
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Paragraph 0289; 0290; 0291; 0292
(2016/10/08)
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- Reduction of 1,2-dicarbonyl compounds and of their N-phenylimine derivatives by sodium cyanide under aprotic conditions
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Some aromatic 1,2-dicarbonyl compounds, i.e. 9,10-phenanthrenequinone, acenaphthenequinone and benzil, and their corresponding N-phenyl monoimines, have been reduced, using dry acetonitrile as the solvent, in the presence of sodium cyanide as a reducing agent. Comparative potentiostatic preparative-scale electrolysis is described.
- Batanero, Belen,Hamrouni, Kaouthar,Barba, Fructuoso,Barba, Isidoro,Boujlel, Khaled,Benkhoud, Mohamed Lamine
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p. 1284 - 1288
(2015/12/12)
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- One-step synthesis of unsymmetrical N -Alkyl- N '-aryl perylene diimides
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An efficient and facile protocol for the synthesis of unsymmetrical N-alkyl-N'-aryl perylene diimides is reported that circumvents the need for multiple reaction steps. A number of unsymmetrical perylene diimides containing a solubilizing swallowtail alky
- Robb, Maxwell J.,Newton, Brandon,Fors, Brett P.,Hawker, Craig J.
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p. 6360 - 6365
(2014/07/21)
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- Versatile and sustainable synthesis of cyclic imides from dicarboxylic acids and amines by Nb2O5 as a base-tolerant heterogeneous lewis acid catalyst
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Catalytic condensation of dicarboxylics acid and amines without excess amount of activating reagents is the most atom-efficient but unprecedented synthetic method of cyclic imides. Here we present the first general catalytic method, proceeding selectively and efficiently in the presence of a commercial Nb2O5 as a reusable and base-tolerant heterogeneous Lewis acid catalyst. The method is effective for the direct synthesis of pharmaceutically or industrially important cyclic imides, such as phensuximide, N-hydroxyphthalimide (NHPI), and unsubstituted cyclic imides from dicarboxylic acid or anhydrides with amines, hydroxylamine, or ammonia.
- Ali, Md. Ayub,Siddiki, S. M. A. Hakim,Kon, Kenichi,Hasegawa, Junya,Shimizu, Kenichi
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supporting information
p. 14256 - 14260
(2015/01/09)
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- Copper-catalyzed direct N-arylation of naphthalimides using diaryliodonium Salts
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An effective copper-catalyzed N-arylation of naphthal-imides with diaryliodonium salts in toluene at 100 °C has been developed. This cross-coupling reaction gives the desired N-arylated 1,8-naphthalimides in moderate to good yields. The synthetic potentia
- Mao, Song,Guo, Fenglou,Li, Juan,Geng, Xu,Yu, Jianjun,Han, Jianwei,Wang, Limin
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p. 1959 - 1962
(2013/09/24)
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- Water-solvent method for the synthesis of N-substituted and N-,4-disubstituted 1,8-naphthalimides under microwave irradiation
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A preparation of a series of N-and N-,4-substituted 1,8-naphthalimides using water as solvent under microwave irradiation, which proceeded via efficient and green reaction of 1,8-naphthalic anhydride derivatives with different amines, is described.
- Zhang, Ye,Feng, Shao-Bo,Wang, Kai,Yi, Xiang-Hui,Wang, Heng-Shan,Pan, Ying-Ming
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experimental part
p. 3042 - 3052
(2012/08/14)
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- Solvent-free synthesis of 1,8-naphthalimide derivatives under microwaves irradiation
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A solvent-free synthesis of a series of 1,8-naphthalimide derivatives, which proceeds via facile, economical and efficient reaction of primary amine with 1,8-naphthalic anhydride derivatives under microwave irradiation, was described.
- Wu, Qiang,Qin, Wen
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scheme or table
p. 4713 - 4714
(2012/02/15)
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- Microwave-assisted synthesis and evaluation of naphthalimides derivatives as free radical scavengers
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A facile and efficient microwave-assisted reaction of 1,8-naphthalic anhydride derivatives with primary amines, leading to the synthesis of 1,8-naphthalimides, has been developed. Subsequently, the free radical scavenging properties of the 1,8-naphthalimide derivatives were evaluated against 2,2-diphenyl-1-picrylhydrazyl (DPPH). The results showed that the scavenging activities of compounds 2a, NBNA, 3b, and 3c were more efficient than that of the common synthetic antioxidant 2,6-diterbutyl- 4-methylphenol (BHT), with IC50 values of 61.9, 54.0, 42.2, and 43.1 μM, respectively. The imide groups introduced at position 4 as well as the nitro functionality at position 3 of the naphthalene moiety were the major contributors to the free radical scavenging activities. Springer Science+Business Media, LLC 2010.
- Zhang, Ye,Feng, Shaobo,Wu, Qiang,Wang, Kai,Yi, Xianghui,Wang, Hengshan,Pan, Yingming
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experimental part
p. 752 - 759
(2012/05/20)
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- Evaluation of apoptotic effect of cyclic imide derivatives on murine B16F10 melanoma cells
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Cyclic imides are a large class of compounds obtained by organic synthesis including several sub-classes (succinimides maleimide, glutarimide, phthalimides naphtalimides, and its derivatives). Recently, some cyclic imide derivatives have shown important results as potential antitumor agents, as a Mitonafide and Amonafide. Based on this fact, we have studied antitumoral properties of nine cyclic imide derivatives, four of which are unpublished compounds, against Murine Melanoma Cells (B16F10). Initially, the MTT assay was used to select the compound with the best cytotoxic potential. After this selection, the compound 2-benzyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (4), which showed the best cytotoxic effects, was evaluated by flow cytometry, and a significant increase was observed in the proportion of cells in the subG0/G1, S and G2/M phases accompanied by a significant decrease in the G0/G1 phases. Then the mechanism involved on the death route (necrosis or apoptosis) was evaluated the by bromide and acridine orange method and by an Annexin V-FITC Apoptosis Detection kit. These results confirm that the percentage of B16F10 cells observed in the sub G0/G1 phase were undergoing apoptosis. The biological effects observed in the current study for the cyclic imide derivatives suggested promising applications, especially for the prototype compound 4.
- Machado, Karina Elisa,De Oliveira, Kely Navakoski,Santos-Bubniak, Lorena,Licínio, Marley Aparecida,Nunes, Ricardo José,Santos-Silva, Maria Cláudia
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experimental part
p. 6285 - 6291
(2011/12/14)
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- Synthesis, anti-inflammatory activity and COX-1/COX-2 inhibition of novel substituted cyclic imides. Part 1: Molecular docking study
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A group of cyclic imides (1-13) was designed for evaluation as selective COX-2 inhibitors and investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw edema model. Compounds 5b, 6b, 11b, 11c, 12b and 12c were proved to be potent COX-2 inhibitors with IC50 range of 0.1-1.0 μM. In vitro COX-1/COX-2 inhibition structure-activity studies identified compound 5b as a highly potent (IC50 = 0.1 μM), and an extremely selective [COX-2 (SI) = 400] comparable to celecoxib [COX-2 (SI) > 333.3], COX-2 inhibitor that showed superior anti-inflammatory activity (ED 50 = 104 mg/kg) relative to diclofenac (ED50 = 114 mg/kg). A Virtual screening was carried out through docking the designed compounds into the COX-2 binding site to predict if these compounds have analogous binding mode to the COX-2 inhibitors. Molecular modeling (docking) study showed that the CH3O substituents of 5b inserted deep inside the 2°-pocket of the COX-2 active site, where the O-atoms of such group underwent a H-bonding interaction with His90 (2.43, 2.83 ), Arg513 (2.89 ) and Tyr355 (3.34 ). Docking study of the synthesized compound 5b into the active site of COX-2 revealed a similar binding mode to SC-558, a selective COX-2 inhibitor.
- Abdel-Aziz, Alaa A.-M.,Eltahir, Kamal E.H.,Asiri, Yousif A.
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scheme or table
p. 1648 - 1655
(2011/05/06)
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- Intermolecular oxidative C-N bond formation under metal-free conditions: Control of chemoselectivity between aryl sp2 and benzylic sp 3 C-H bond imidation
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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
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supporting information; experimental part
p. 16382 - 16385
(2011/12/13)
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- Metal-free intermolecular oxidative C-N bond formation via tandem C-H and N-H bond functionalization
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The development of a novel intermolecular oxidative amination reaction, a synthetic transformation that involves the simultaneous functionalization of both a N-H and C-H bond, is described. The process, which is mediated by an I(III) oxidant and contains no metal catalysts, provides a rapid and green method for synthesizing protected anilines from simple arenes and phthalimide. Mechanistic investigations indicate that the reaction proceeds via nucleophilic attack of the phthalimide on an aromatic radical cation, as opposed to the electrophilic aromatic amination that has been reported for other I(III) amination reactions. The application of this new reaction to the synthesis of a variety of substituted aniline derivatives is demonstrated.
- Kantak, Abhishek A.,Potavathri, Shathaverdhan,Barham, Rose A.,Romano, Kaitlyn M.,Deboef, Brenton
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supporting information; experimental part
p. 19960 - 19965
(2012/01/13)
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- Comparison of microwave-assisted and conventional preparations of cyclic imides
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Microwave-assisted preparation of several cyclic imides was performed with four different cyclic anhydrides. All the reactions are significantly faster and the isolated yields are significantly higher compared to conventionally heated reactions. Furthermore, many of these reactions can be performed with a minimal amount of solvent, thereby enabling the synthetic chemist to obtain high quantities of pure cyclic imides in a matter of hours.
- Upadhyay, Sunil K.,Pingali, Subramanya R.K.,Jursic, Branko S.
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experimental part
p. 2215 - 2217
(2010/05/18)
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- A novel donor-acceptor polymeric electrochromic material containing carbazole and 1,8-naphtalimide as subunit
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We report here the synthesis of a novel polymeric electrochromic material containing carbazole (Cbz)-donor and 1,8-napthalimide-acceptor as subunit. The band gap Eg was measured using UV-vis spectroscopy and compared with that obtained by cyclic voltammetry (CV). Due to intramolecular electron transfer from Cbz-donor to 1,8-napthalimide-acceptor, the fluorescence quenching was observed. When the spectro-electrochemical and electrochromic properties of polymer film were investigated, various tones of green color were obtained on the polymeric film. In the positive regime, the polymer film obtained thereby is dark green resulting from the association of carbazolylium cation radicals at oxidized state and then it can be bleached by electrochemical reduction. Besides, in the negative regime, yellowish green color of film converted to blue attributed to reduction of the 1,8-napthalimide moiety. Finally, the polymeric electrochromic exhibits multi-electrochromic behavior, high redox stability, high coloration efficiency and reasonable response time.
- Koyuncu, Fatma Baycan,Koyuncu, Sermet,Ozdemir, Eyup
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experimental part
p. 4935 - 4941
(2010/09/06)
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- Facile synthesis of 1,8-naphthalimides in palladium-catalysed aminocarbonylation of 1,8-diiodo-naphthalene
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1,8-Diiodo-naphthalene was aminocarbonylated with various primary and secondary amines in the presence of palladium(0) complexes formed in situ from palladium(II) acetate and triphenylphosphine. In the case of primary amines, depending on the amine to substrate ratio, two types of products have been obtained in highly chemoselective reaction: dicarboxamides and N-substituted imides have been formed at high and low amine to substrate ratio, respectively. The reaction tolerates the ester functionality, so that amino acid esters could serve as N-nucleophiles and in this way, naphthalimides possessing stereogenic centre in the N-substituent could be synthesised.
- Takács, Attila,ács, Péter,Kollár, László
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p. 983 - 987
(2008/09/18)
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- Photoinduced energy and electron transfer in 1,8-naphthalimide-corrole dyads
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A series of corrole-1,8-naphthalimide dyads has been synthesized. The dyads were assembled in a convergent fashion from two fragments via a corrole forming reaction. Central to the success of the synthetic strategy was the preparation of suitably functionalized derivatives of naphthalene-1,8-carboxymide. Six different dyads possessing either a different linker (a meta-phenylene or a para-phenylmethylene) or a corrole with different substituents at the 5 and 15 positions were prepared. A photophysical and spectroscopic characterization of the dyads and the reference models show that whereas upon selective excitation of the corrole component no photo-induced process occurs, excitation of the naphthalimide unit results in very efficient energy or electron transfer processes. The electron transfer contributes to the quenching process with a ratio between 0% and 85% depending on the nature of the corrole accepting unit. The processes are discussed in the frame of current theories. This is the first report of stable corrole-based dyads with interesting photo-activity at ambient temperature. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
- Tasior, Mariusz,Gryko, Daniel T.,Cembor, Marek,Jaworski, Jan S.,Ventura, Barbara,Flamigni, Lucia
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p. 247 - 259
(2008/02/02)
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- Toward intrinsically fluorescent proteomimetics: Fluorescent probe response to alpha helix structure of poly-γ-benzyl-l-glutamate
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A fluorescent probe (1), developed for recognition of alpha helical secondary structure, shows a large fluorescence change upon titration with the synthetic protein PBLG. Compared to fluorophores of similar size and shape, 1 displayed the smallest dissoci
- Hutt, Kenji,Hernandez, Randy,Heagy, Michael D.
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p. 5436 - 5438
(2007/10/03)
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- Matrix screening of substituted N-aryl-1,8-naphthalimides reveals new dual fluorescent dyes and unusually bright pyridine derivatives
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A 3 × 14 matrix of substituted N-aryl-1,8-naphthalimides was synthesized for the evaluation and discovery of dual fluorescence. Because of their unique photophysical properties, these dual fluorescent systems represent an exception to the widely studied T
- Cao, Haishi,Chang, Virginia,Hernandez, Randy,Heagy, Michael D.
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p. 4929 - 4934
(2007/10/03)
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- Copper-promoted N-arylations of cyclic imides within six-membered rings: A facile route to arylene-based organic materials
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(Chemical Equation Presented) Cyclic imides within six-membered rings are shown to undergo efficient N-arylation using various arylboronic esters mediated by copper(II) acetate in the presence of an amine base and oxygen atmosphere with gentle heating. Until now, the synthesis of N-arylated cyclic imides having six-membered rings was restricted largely to strongly heating anilines in the presence of anhydrides. This reaction is applicable to the synthesis of new organic materials based on arylene imide and bis(imide) dyes, such as perylene-3,4: 9,10-bis(dicarboximide)s.
- Chernick, Erin T.,Ahrens, Michael J.,Scheidt, Karl A.,Wasielewski, Michael R.
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p. 1486 - 1489
(2007/10/03)
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- A "green" route to perylene dyes: Direct coupling reactions of 1,8-naphthalimide and related compounds under mild conditions using a "new" base complex reagent, t-BuOK/DBN
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The direct coupling reactions of 1,8-naphthalimide compounds efficiently occurred at 130 or 170 °C without the intervention of the leuco form dyes in the presence of base complex reagent, t-BuOK/1,5-diazabicyclo[4.3.0]non-5-ene (DBN), to give the corresponding perylene dyes in good yields with >95% purities. A possible mechanistic speculation for these oxidative coupling reactions is briefly discussed.
- Sakamoto,Pac
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- Analgesic activity of cyclic imides: 1,8-Naphthalimide and 1,4,5,8- naphthalenediimide derivatives
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In early studies, we have reported the synthesis and biological activities of several cyclic imides. The present study describes the analgesic activity of 1,8-naphthalimide and 1,4,5,8-naphthalenediimide derivatives in a standard murine model of analgesia. The pharmacological results show that all compounds studied, given intraperitoneally, produced significant inhibition of acetic acid-induced abdominal constrictions. At the ID50 (μmol/kg) level, these cyclic imide derivatives were about 40-270- fold more potent in this assay than aspirin and acetaminophen, two well-known and widely used analgesics. These results extend previous studies on the analgesic activity of cyclic imides. (C) 2000 Elsevier Science S.A.
- Andricopulo, Adriano Defini,Mueller, Luciane A.,Cechinel Filho, Valdir,Cani, Graziela S.,Roos, Juliana F.,Correa, Rogerio,Santos, Adair Roberto S.,Nunes, Ricardo Jose,Yunes, Rosendo Augusto
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p. 319 - 321
(2007/10/03)
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- Perylene derivatives formation in reaction of 3-bromobenzanthrone and 4-bromonaphthalic acid derivatives with a reduction system NiCl2 - 2,2′bipyridyl (or 1,10-phenathroline) - Zn
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The reaction of 3-bromobenzanthrone and 4-bromonaphthalic acid derivatives with a reduction system NiCl2-2,2′bipyridyl (or 1,10-phenathroline)-Zn gives rise to compounds containing perylene fragment. Under similar conditions was established a possibility to transform substituted 1,1′-binaphthyls into the corresponding perylene derivatives.
- Adonin,Ryabinin,Starichenko
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p. 861 - 865
(2007/10/03)
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- Imidyl Radicals. The Chemistries of 1,8-Naphthalenedicarboximidyl and Phthalimidyl Radicals
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The chemistries of 1,8-naphthalenedicarboximidyl (N.) and phthalimidyl (P.) radicals are described.Hydrogen abstractions from alkanes and additions to olefins and benzene proceed in high yield.The low cost of phthalimide, coupled with the absence of a parasitic ring-opening reaction for P., makes N-bromophthalimide an economical reagent for low-selectivity brominations.The chemistry of N. resembles that of other imidyl radicals (succinimidyl, glutarimidyl) with respect to selectivities.Conversely, P. is somewhat of a maverick among imidyl radicals, being slightly more selective in its reactions, but still 102-103 less selective than Br..
- Day, J. C.,Govindaraj, N.,McBain, D. S.,Skell, P. S.,Tanko, J. M.
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p. 4959 - 4963
(2007/10/02)
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- N-SUBSTITUTED ISONAPHTHALIMIDES. FORMATION AND REACTION WITH AMINES
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N-Substituted isonaphthalimides and N-substituted naphthalimides, as considered previously, are formed in the reaction of 1,8-naphthaloyl chloride with primary amines.The reaction of N-substituted isonaphthalimides with sterically unhindered amines leads to the N,N'-substituted diamides of 1,8-naphthalenedicarboxylic acid.In the case of sterically hindered amines it results in isomerization to the N-substituted naphthalimides.The thermolysis of the N,N'-substituted diamides of 1,8-naphthalenedicarboxylic acid leads to amines and N-substituted naphthalimides.
- Ganin, E. V.,Makarov, V. F.,Nikitin, V. I.
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p. 2209 - 2215
(2007/10/02)
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- SYNTHESES AND PROPERTIES OF SOME DERIVATIVES OF N--NAPHTHALIMIDE
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Syntheses of N--naphthalimide and N--naphthalimide derivatives, unreported so far in the literature have been worked out, and the products are characterized.The usefulness of some of them as optical brightening agents has been established from their fluorescence spectra.The phenomenon of an intramolecular energy transfer from the benzotriazole to naphthalimide ring systems has been observed for the derivatives of N--naphthalimide.
- Jankowski, Zdzislaw,Stolarski, Roland
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p. 555 - 564
(2007/10/02)
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