- Substituent effect of ancillary ligands on the luminescence of bis[4,6-(di-fluorophenyl)-pyridinato-N,C2′]iridium(iii) complexes
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Two series of (dfppy)2Ir(LN^O) with different substituents were designed and successfully synthesized and the effect of substitution at the ancillary ligand on the photophysical and electrochemical properties of (dfppy)2Ir
- Zhou, Yuyang,Li, Wanfei,Liu, Yang,Zeng, Liqiang,Su, Wenming,Zhou, Ming
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Read Online
- One-Pot Synthesis of Benzo[4,5]imidazo[1,2-a]pyrimidin-2-ones Using a Hybrid Catalyst Supported on Magnetic Nanoparticles in Green Solvents
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The conversion of soluble polyoxometalate into insoluble polyoxometalate is considered to be one of the major challenges in synthetic organic chemistry. Here, polyoxometalate was bonded to the salt part of an organic branch immobilized on the silica-coate
- Moussa, Alkassoume,Rahmati, Abbas
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Read Online
- Base-Catalyzed Tandem Cyclization: Diastereoselective Access to the 3,4-Dihydroisoquinolin-2(1 H)-one Core
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A novel, one-pot reaction for the synthesis of 3,4-dihydroisoquinolin-2(1 H)-one derivatives is developed via a base-mediated three-component reaction of ninhydrin, aniline and acetylenic esters. This diastereoselective reaction takes place in methanol at 70A °C under transition-metal-free conditions, and direct construction of the C-N and C-C bonds is readily achieved via tandem cyclization. These cyclic frameworks are resourceful small molecular keys to many natural products.
- Shirsat, Prashishkumar K.,Khomane, Navnath B.,Meshram, Sneha H.,Sridhar, Balasubramanian,Meshram, Harshadas M.,Kumbhare, Ravindra M.
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Read Online
- Synthesis, crystal structure and dft studies of polyfunctionalized alkenes: A transition metal-free c(sp2)-h sulfenylation of electron deficient alkyne
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An efficient, novel and transition metal-free protocol has been developed for the synthesis of polyfunctionalized aminothioalkenes via direct C[sbnd]H sulfenylation of in situ generated enamines. The reaction was performed using a catalytic amount of inex
- Khurana, J. M.,Kumar, Parvin,Saroha, Mohit,Sindhu, Jayant
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Read Online
- Trifluoroacetic acid catalyzed one-pot four-component domino reaction for the synthesis of substituted dihydro 2-oxypyrroles
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Trifluoroacetic acid was applied as an effcient catalyst for the one-pot four-component synthesis of N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates via the domino reaction of amines, formaldehyde and dialkyl acetylenedicarboxylates at ambient temp
- Lashkari, Mojtaba,Maghsoodlou, Malek Taher,Karima, Mahsa,Kangani, Mehrnoosh
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Read Online
- The synthesis of quinolone natural products from pseudonocardia sp.
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The synthesis of four quinolone natural products from the actinomycete Pseudonocardia sp. is reported. The key step involved a sp2-sp3 Suzuki-Miyaura reaction between a common boronic ester lateral chain and various functionalised quinolone cores. The quinolones slowed growth of E. coli and S. aureus by inducing extended lag phases. The total synthesis of four quinolone natural products is reported. The quinolones were synthesised in a highly efficient and direct manner from various readily prepared quinolone cores and a common boronic ester lateral chain. The key step involved a challenging sp2-sp3 Suzuki-Miyaura reaction.
- Salvaggio, Flavia,Hodgkinson, James T.,Carro, Laura,Geddis, Stephen M.,Galloway, Warren R. J. D.,Welch, Martin,Spring, David R.
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Read Online
- Synthesis of Natural and Unnatural Quinolones Inhibiting the Growth and Motility of Bacteria
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Synthesis of a recently discovered S-methylated quinolone natural product (1) was carried out, in addition to the production of a range of 2-substituted 4-quinolone derivatives (2-11). Two approaches were used: (i) the base-catalyzed cyclization of N-(ket
- Li, Jianye,Clark, Benjamin R.
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p. 3181 - 3190
(2020/11/03)
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- Synthesis of new polyaryl-substituted imidazoles bridged on enamine or urea moieties and evaluation of their optical and electrochemical properties
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Abstract: The reaction of the free amine group in polyaryl-substituted imidazole structures with phenyl isocyanate or dimethyl acetylenedicarboxylate gave two new series of polyaryl-substituted imidazoles: biaryl ureas or vinyl esters, respectively. Besid
- Fakhree, Ameneh Abolghassemi,Mohammadzadeh, Roghayeh,Alipour, Esmaeel,Ghasemi, Zarrin
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p. 2069 - 2082
(2020/01/21)
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- One-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed three-component cascade annulation of amines, alkyne esters and terminal alkynes
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Described herein is a new and general method for one-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed [3 + 1 + 2] annulation of simple amines, alkyne esters and terminal alkynes. The versatile transformation might initiate with the facil
- Li, Yunlan,Zhang, Qiurui,Xu, Xuefeng,Zhang, Xu,Yang, Yurong,Yi, Wei
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supporting information
p. 965 - 970
(2019/03/13)
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- Stereoselective Aminoiodination of Activated Alkynes with Organoiodine(III) Reagents and Amines via Multiple-Site Functionalization: Access to Iodinated Enamines and N-Aryl Indoles
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A stereoselective aminoiodination of activated alkynes with PhI(OAc)2 and amines via multiple-site functionalization to afford (Z)diethyl 2-(diphenylamino)-3-iodomaleate derivatives with superior yields has been described. The key feature of th
- Arepally, Sagar,Chamuah, Ajoy,Katta, Narenderreddy,Sharada, Duddu S.
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supporting information
p. 1542 - 1547
(2019/02/03)
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- Novel One-Pot Synthesis of Functionalized Quinolines from Isocyanides, Aniline, and Acetylene Dicarboxylate via Cu-Catalyzed Intramolecular C─H Activation Reactions
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The one-pot synthesis of a novel class of substituted quinoline derivatives with good yields is achieved via the Cu-catalyzed intramolecular C─H activation reaction between isocyanides, aniline, and acetylene dicarboxylate in MeCN at room temperature. The
- Nematpour, Manijeh,Rezaee, Elham,Jahani, Mehdi,Tabatabai, Sayyed Abbas
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p. 1254 - 1259
(2019/03/07)
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- Application and developing of iron-doped multi-walled carbon nanotubes (Fe/MWCNTs) as an efficient and reusable heterogeneous nanocatalyst in the synthesis of heterocyclic compounds
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Iron-doped multi-walled carbon nanotubes (Fe/MWCNTs) is an efficient, ecofriendly and reusable heterogeneous nanocatalyst for the one-pot synthesis of heterocyclic compounds including bis-spiro piperidines, piperidines, dihydro-2-oxopyrroles, pyrazoles and diazepines at room temperature with good to excellent yields. The heterogeneous nanocatalyst was fully characterized by scanning electron microscopy (SEM), X-ray diffraction (XRD), inductively coupled plasma (ICP) and FT-IR analysis. Also, the structures of all prepared compounds were characterized by 1H NMR, 13C NMR, FT-IR, mass spectrometry (MS) and elemental analysis. The major advantages of these protocols are mild and green reaction conditions, short reaction times, clean reaction, operational simplicity, easy purification and good to excellent yields with the reusable heterogeneous nanocatalyst. The catalyst was ten recycled without significant loss of activity.
- Sharghi, Hashem,Aboonajmi, Jasem,Mozaffari, Mozhdeh,Doroodmand, Mohammad Mahdi,Aberi, Mahdi
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- A three-component one-pot synthesis of penta-substituted pyrroles via ring opening of α-nitroepoxides
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A novel and facile one-pot reaction has been developed to synthesize a variety of penta-substituted pyrroles from α-nitroepoxides, primary amines and dialkyl acetylenedicarboxylates under the conditions without catalyst. Furthermore, the controlled experi
- Zhao, Donghong,Zhu, Yue,Guo, Shanshan,Chen, Wenteng,Zhang, Guolin,Yu, Yongping
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supporting information
p. 2872 - 2877
(2017/04/26)
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- One-pot synthesis and structure∑property relationship of aminomaleimides: Fluorescence efficiencies in monomers and aggregates easily tuned by switch of aryl and alkyl
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Organic fluorophores have attracted great interest owing to their wide applications. They usually contain an electron-conjugated system with an aromatic moiety and show high emission in dilute solutions but weaker or even no emission upon aggregation. Her
- Zhu, Qiuhua,Ye, Ziwei,Yang, Weijie,Cai, Xiaotie,Tang, Ben Zhong
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p. 1096 - 1104
(2018/05/14)
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- Hypervalent iodine(III)-promoted: N -incorporation into N -aryl vinylogous carbamates to quinoxaline diesters: Access to 1,4,5,8-tetraazaphenanthrene
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A novel oxidative N-incorporation strategy for synthesis of quinoxaline diesters under metal-free conditions is described for the first time. The mild reaction conditions allow for this transformation via the formation of two C(sp2)-N bonds utilizing cheaply available NaN3 as the N-atom source. N-Aryl vinylogous carbamates in this study undergo azidation at enamino C(sp2)-H selectively. The robustness of this strategy is further demonstrated by the synthesis of a valuable 1,4,5,8-tetraazaphenanthrene derivative using a mild and convenient approach.
- Sagar,Vidaycharan, Shinde,Shinde, Anand H.,Sharada, Duddu S.
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supporting information
p. 4018 - 4022
(2016/06/14)
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- Regioselective Synthesis of 2,3,4-Trisubstituted Pyrroles via Pd(II)-Catalyzed Three-Component Cascade Reactions of Amines, Alkyne Esters, and Alkenes
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A new, efficient, and versatile Pd(II)-catalyzed oxidative three-component cascade reaction of diverse amines, alkyne esters, and alkenes is disclosed for the direct synthesis of diverse 2,3,4-trisubstituted pyrroles with broad functional group tolerance and in good to excellent yields. This transformation is supposed to proceed through the cascade formation of C(sp2)-C(sp2) and C(sp2)-N bonds via Pd(II)-catalyzed regioselective alkene migratory insertion, intramolecular radical addition, and oxidation sequential processes.
- Zhang, Xu,Xu, Xuefeng,Chen, Gong,Yi, Wei
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supporting information
p. 4864 - 4867
(2016/10/18)
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- Copper(I)-catalyzed one-pot synthesis of highly functionalized pyrrolidines from sulfonyl azides, alkynes, and dimethyl 2-(phenylamino)maleate
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An efficient one-pot synthesis of highly functionalized pyrrolidines by using sulfonyl azides, alkynes, and dimethyl 2-(phenylamino)maleate catalyzed by copper(I)-Y zeolite under mild reaction conditions was investigated. This cascade process involves an azide-alkyne [3+2] cycloaddition/ring rearrangement/ketenimine formation/intermolecular nucleophilic addition cascade and consequent intramolecular cyclization followed by [1,3]-H shift. The important advantage of this methodology, which allows selective intramolecular nucleophilic attack of the generated ketenimine carbanion on an ester moiety for the first time, is that the starting materials can be easily prepared.
- Ramanathan, Devenderan,Pitchumani, Kasi
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supporting information
p. 463 - 467
(2015/01/30)
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- Synthesis of fused pyrrolo[3,4-d]tetrahydropyrimidine derivatives by proline-catalyzed multicomponent reaction
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Novel proline-catalyzed multicomponent reactions (MCRs) for the synthesis of fused pyrrolo[3,4-d]tetrahydropyrimidines 7 and 9 with different substituted patterns have been developed, which provide rapid access to a library of compounds 7 and 9 in medium to excellent yields, by using N-methyl-α- aryl(alkyl)aminomaleimides, amines, and aldehydes as reactants. The catalyst and the ratio of reactants were found to have significant impact on these reactions, and a reasonable mechanism was also proposed.
- Chen, Zhi-Peng,Wang, Hai-Bo,Wang, Yu-Qin,Zhu, Qiu-Hua,Xie, Yang,Liu, Shu-Wen
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supporting information
p. 4379 - 4385
(2014/06/10)
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- Synthesis of functionalized 2-pyridones via Michael addition and cyclization reaction of amines, alkynes and dialkyl acetylene dicarboxylates
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The Michael addition and three-component cyclization reaction of amines, alkynes and dialkyl acetylene dicarboxylates to form pyridones has been developed. Aliphatic amines and aromatic amines could selectively be converted into N-alkyl-disubstituted 2-pyridones and N-aryl-trisubstituted 2-pyridones with good yields in the presence of wet ethanol, which means a suitable amount of water is required for this reaction. The Michael addition and cyclization reaction process was confirmed through deuterium-labeling experiments, intermediates isolation and control experiments. The Royal Society of Chemistry 2013.
- Chong, Qinglei,Xin, Xiaoyi,Wang, Chunxiang,Wu, Fan,Wan, Boshun
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p. 21222 - 21226
(2013/11/06)
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- A one-pot multi-component synthesis of N-aryl-3-aminodihydropyrrol-2-one-4- carboxylates catalysed by oxalic acid dihydrate
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A simple synthesis of N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates via one-pot multi-component reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde in the presence of oxalic acid dihydrate (20 mol%) as catalyst in methanol is described
- Sajadikhah, Seyed Sajad,Hazeri, Nourallah,Maghsoodlou, Malek Taher,Mostafa, Sayyed,Habibi-Khorassani,Khandan-Barani, Khatereh
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- Efficient synthesis of the functionalized spiro[indoline-3,4'-pyridine] via four-component reaction
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An efficient synthetic procedure for the functionalized spiro[indoline-3,4'-pyridine] was developed via the four-component reactions of arylamines, acetylenedicarboxylates, isatins and malononitrile with triethylamine as the base catalyst. The advantages
- Sun, Jing,Wu, Qun,Zhang, Lijuan,Yan, Chaoguo
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experimental part
p. 1548 - 1554
(2012/09/07)
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- Solvent-free synthesis of enamines from alkyl esters of propiolic or but-2-yne dicarboxylic acid in a ball mill
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A solvent-free method for the addition of amines to dialkylacetylendicarboxylates or alkylpropiolates using a planetary ball mill was developed. Conversion of educts was quantitative within five minutes without use of any catalyst or base. Beside the E-/Z
- Thorwirth, Rico,Stolle, Achim
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scheme or table
p. 2200 - 2202
(2011/11/06)
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- Selective synthesis of fused 1,4-and 1,2-dihydropyridines by domino reactions of arylamines, acetylenedicarboxylate, aldehydes, and cyclic 1,3-diketones
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A practical procedure for the preparation of fused 1,4-dihydropyridines was developed through the domino four-component reactions of arylamines, acetylenedicarboxylate, aromatic aldehydes, and cyclic 1,3-diketones in acetic acid. Unusual fused 1,2-dihydropyridines can also be efficiently prepared by controlling the reaction conditions.
- Sun, Jing,Sun, Yan,Gao, Hong,Yan, Chao-Guo
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experimental part
p. 6952 - 6956
(2012/01/06)
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- Synthesis and pharmacological evaluation of some 4-Oxo-quinoline-2- carboxylic acid derivatives as anti-inflammatory and analgesic agents
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The synthesis and the pharmacological activity of a series of 1-aroyl derivatives of kynurenic acid methyl ester (4-oxo-quinolin-2-carboxy methyl (KYNA) esters), structurally related to NSAID indomethacin are described. The derivatives were screened in vi
- Mazzoni, Orazio,Esposito, Giovanni,Diurno, Maria Vittoria,Brancaccio, Diego,Carotenuto, Alfonso,Grieco, Paolo,Novellino, Ettore,Filippelli, Walter
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experimental part
p. 561 - 569
(2011/06/21)
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- Practical synthesis and mechanistic study of polysubstituted tetrahydropyrimidines with use of domino multicomponent reactions
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The practical synthesis of polysubstituted tetrahydropyrimidines 4 from but-2-ynedioates 1, amines 2, and formaldehyde 3 through a domino process of one-pot multicomponent reactions (MCRs) and the detailed mechanistic studies are described. The MCRs were
- Zhu, Qiuhua,Jiang, Huanfeng,Li, Jinghao,Zhang, Min,Wang, Xiujun,Qi, Chaorong
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experimental part
p. 4604 - 4613
(2009/10/02)
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- Synthesis of aza-Henry products and enamines in water by Michael addition of amines or thiols to activated unsaturated compounds
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Nitroamines and nitrothiols were synthesized in high yields by the Michael addition of amines and thiols to nitroolefins without using any catalyst. Also, the reaction of amines with dimethylacetylene dicarboxylate (DMAD) in water afforded the corresponding enamines.
- Ziyaei-Halimehjani, Azim,Saidi, Mohammad R.
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p. 1244 - 1248
(2008/09/17)
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- PROCESS FOR THE PREPARATION AND PHARMACEUTICAL FORMULATIONS FOR 4-QUINOLINONES AND QUINOLINES AND USE THEREOF
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The present invention describes novel 4-quinolinones corresponding to formula (I) and quinoline derivatives thereof as formula (II), process of preparation thereof, pharmaceutical formulations comprising said 4-quinolinones and pharmaceutical application
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Page/Page column 8; 13-14
(2009/01/20)
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- Kynurenic acid amides as novel NR2B selective NMDA receptor antagonists
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A novel series of kynurenic acid amides, ring-enlarged derivatives of indole-2-carboxamides, was prepared and identified as in vivo active NR2B subtype selective NMDA receptor antagonists. The synthesis and SAR studies are discussed.
- Borza, Istvan,Kolok, Sandor,Galgoczy, Kornel,Gere, Aniko,Horvath, Csilla,Farkas, Sandor,Greiner, Istvan,Domany, Gyoergy
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p. 406 - 409
(2007/10/03)
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- A synthesis of 4-quinolone-3-carboxylic acids via pyrolysis of N- aryldioxopyrrolines
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A synthesis of 4-quinolone-3-carboxylic acids (8) was achieved by pyrolysis of 4,5-dimethoxycarbonyl-1-aryl-1H-pyrrole-2,3-diones (3) followed by selective demethoxycarbonylation of the resulting 2,3-dimethoxycarbonyl-4- quinolones (4) in excellent overall yields.
- Mohri, Kunihiko,Kanie, Akihiko,Horiguchi, Yoshie,Isobe, Kimiaki
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p. 2377 - 2384
(2007/10/03)
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- Novel β-iminoenolato ( or β-carbonyliminato) complexes starting from di-μ-hydroxo palladium or platinum complexes with dimethyl acetylenedicarboxylate and primary amines: Crystal structure of [NBu4][(C6F5) 2Pd{N
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The reaction of the binuclear hydroxo complexes [NBu4]2[{M(C6F5)2(μ-OH)}2] (M = Pd or Pt) with alkyl or arylamines (RNH2) in the presence of dimethyl acetylenedicarboxylate (DMAD
- Ruiz, Jose,Rodriguez, Venancio,Lopez, Gregorio,Chaloner, Penny A.,Hitchcock, Peter B.
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- 2-Carboxytetrahydroquinolines. Conformational and Stereochemical Requirements for Antagonism of the Glycine Site on the NMDA Receptor
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2-Carboxy-1,2,3,4-tetrahydroquinoline derivatives, derived from kynurenic acid, have been synthesized and evaluated for in vitro antagonist activity at the glycine site on the NMDA receptor. 2,3-Dihydrokynurenic acids show reduced potency relative to the
- Carling, Robert W.,Leeson, Paul D.,Moseley, Angela M.,Baker, Raymond,Foster, Alan C.,et al.
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p. 1942 - 1953
(2007/10/02)
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- Alkyl esters of substituted 2-methyl-3-quinolinecarboxylic acid and quinoline-2,3-dicarboxylic acid: dialkyl 3-(substituted)phenylaminobut-2-ene-dioates and methods for the preparation thereof
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There are provided novel alkyl esters of substituted 2-methyl-3-quinolinecarboxylic acid and quinoline-2,3-dicarboxylic acid; novel dialkyl 3-(substituted)phenylaminobut-2-ene-dioates, useful as intermediates for the preparation of highly effective 2-(2-imidazolin-2-yl)quinoline herbicidal agents and methods for the preparation thereof.
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- Mechanism of hydrolysis and structure-stability relationship of enaminones as potential prodrugs of model primary amines
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The objective of this work was to investigate the chemistry and the structure-stability relationship of enaminones (a class of enamines formed between a primary amine and a 1,3-dicarbonyl compound) and to evaluate their potential usefulness as prodrugs of primary amines. The acid-catalyzed degradation of the enaminones was found to be very sensitive to minor differences in the structure of the 1,3-dicarbonyl compound used to form the enaminone, but relatively insensitive to changes in the amine portion of the enaminones. A correlation was found between the rate of enaminone hydrolysis and the pK(a) of the 1,3-dicarbonyl compound, suggesting that the rate-controlling step in the hydrolysis of the enaminones was the proton addition to the vinyl carbon of the enaminone. Enaminones formed with cyclic 1,3-dicarbonyl compounds were significantly more stable than those formed with structurally similar acyclic compounds. Based on chemical stability considerations alone, enaminones do not appear to be good candidates as prodrugs of primary amines. Evidence is presented, however, that enaminones formed between amines and 1,3-ketoesters or lactones may be subject to enzyme-catalyzed degradation. Further research on the design of enaminones destabilized by a triggering enzymatic event that results in the loss of conjugation (e.g., ester or lactone hydrolysis or an oxidation/reduction event) may prove worth pursuing.
- Naringrekar,Stella
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p. 138 - 146
(2007/10/02)
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- Alkyl esters of substituted 2-methyl-3-quinolinecarboxylic acid and quinoline-2,3-dicarboxylic acid
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There are provided novel alkyl esters of substituted 2-methyl-3-quinolinecarboxylic acid and quinoline-2,3-dicarboxylic acid; novel dialkyl 3-(substituted)phenylaminobut-2-ene-dioates, useful as intermediates for the preparation of highly effective 2-(2-imidazolin-2-yl)quinoline herbicidal agents and methods for the preparation thereof.
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- 2-(2-imidazolin-2-yl)-pyridines and quinolines, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents
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There are provided novel 2-(2-imidazolin-2-yl)pyridine and quinoline compounds, a process and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.
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