- Ruthenium- and osmium-arene complexes of 8-substituted indolo[3,2-c] quinolines: Synthesis, X-ray diffraction structures, spectroscopic properties, and antiproliferative activity
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Six novel ruthenium(II)- and osmium(II)-arene complexes with indoloquinoline modified ligands containing methyl and halo substituents in position 8 of the molecule backbone have been synthesised and comprehensively characterised by spectroscopic methods (1H, 13C NMR, UV-Vis), ESI mass spectrometry and X-ray crystallography. Binding of indoloquinolines to a metal-arene scaffold makes the products soluble enough in biological media to allow for assaying their antiproliferative activity. The complexes were tested in three human cancer cell lines, namely A549 (non-small cell lung cancer), SW480 (colon carcinoma) and CH1 (ovarian carcinoma), yielding IC50 values in the 10-6-10-7 M concentration range after continuous exposure for 96 h. Compounds with halo substituents in position 8 are more effective cytotoxic agents in vitro than the previously reported species halogenated in position 2 of the indoloquinoline backbone. High antiproliferative activity of both series of substances may be due at least in part to their potential to act as DNA intercalators.
- Filak, Lukas K.,G?schl, Simone,Hackl, Stefanie,Jakupec, Michael A.,Arion, Vladimir B.
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- Electrophilically activated nitroalkanes in synthesis of 3,4-dihydroquinozalines
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Nitroalkanes activated with polyphosphoric acid serve as efficient electrophiles in reactions with various nucleophilic amines. Strategically placed second functionality allows for the design of annulation reactions enabling preparation of various heterocycles. This strategy was employed to develop an innovative synthetic approach towards 3,4-dihydroquinazolines from readily available 2-(aminomethyl)anilines.
- Aksenov, Alexander V.,Aksenov, Dmitrii A.,Aksenov, Nicolai A.,Grishin, Igor Yu.,Malyuga, Vladimir V.,Nobi, Mezvah A.,Rubin, Michael
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- A State-of-the-Art Heterogeneous Catalyst for Efficient and General Nitrile Hydrogenation
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Cobalt-doped hybrid materials consisting of metal oxides and carbon derived from chitin were prepared, characterized and tested for industrially relevant nitrile hydrogenations. The optimal catalyst supported onto MgO showed, after pyrolysis at 700 °C, magnesium oxide nanocubes decorated with carbon-enveloped Co nanoparticles. This special structure allows for the selective hydrogenation of diverse and demanding nitriles to the corresponding primary amines under mild conditions (e.g. 70 °C, 20 bar H2). The advantage of this novel catalytic material is showcased for industrially important substrates, including adipodinitrile, picolinonitrile, and fatty acid nitriles. Notably, the developed system outperformed all other tested commercial catalysts, for example, Raney Nickel and even noble-metal-based systems in these transformations.
- Formenti, Dario,Mocci, Rita,Atia, Hanan,Dastgir, Sarim,Anwar, Muhammad,Bachmann, Stephan,Scalone, Michelangelo,Junge, Kathrin,Beller, Matthias
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supporting information
p. 15589 - 15595
(2020/10/02)
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- Cobalt pincer complexes for catalytic reduction of nitriles to primary amines
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Various cobalt pincer type complexes 1-6 were applied for the catalytic hydrogenation of nitriles to amines. Among these, catalyst 4 is the most efficient, allowing the reduction of aromatic as well as aliphatic nitriles in moderate to excellent yields.
- Schneek?nig, Jacob,Tannert, Bianca,Hornke, Helen,Beller, Matthias,Junge, Kathrin
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p. 1779 - 1783
(2019/04/27)
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- Preparation of a magnetic mesoporous Fe3O4-Pd@TiO2 photocatalyst for the efficient selective reduction of aromatic cyanides
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Herein, a hierarchical magnetic mesoporous microsphere was successfully prepared as a photocatalyst via a simple and reproducible route. Typically, Pd nanoparticles (NPs) were evenly dispersed on the surface of a magnetic Fe3O4 microsphere and then coated with a porous anatase-TiO2 shell to form Fe3O4-Pd@TiO2. The core-shell structure could efficiently suppress the conglomeration of Pd NPs during the calcination process at high temperatures as well as the shedding of Pd during the catalytic reaction process in the liquid phase. The as-prepared photocatalyst was characterized by TEM, XRD, XPS, VSM, and N2 adsorption-desorption. Fe3O4-Pd@TiO2 exhibits high photocatalytic activity for the selective reduction of aromatic cyanides to aromatic primary amines in an acidic aqueous solution. Moreover, this magnetic photocatalyst could be easily recovered from the reaction mixture by an external magnet and reused five times without significant reduction in its activity. The superior photocatalytic efficiency of the proposed photocatalyst may be attributed to its high charge separation efficiency and charge transfer rate, which are caused by the Schottky junction and large interface area. The results indicate that the strategy of coating the active noble metal sites with a mesoporous semiconductor shell has a significant potential for application in metal-semiconductor-based photocatalytic reactions.
- Zhao, Ziming,Long, Yu,Luo, Sha,Wu, Wei,Ma, Jiantai
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p. 6294 - 6302
(2019/04/25)
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- Eco-friendly reactions in PEG-400: A highly efficient and green approach for stereoselective access to multisubstituted 3,4-dihydro-2(1: H)-quinazolines using 2-aminobenzylamines
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An efficient and stereoselective synthesis of novel 3,4-dihydro-2(1H)-quinazolines has been developed through cyclization reactions of 2-aminobenzylamines with α-oxoketene dithioacetals using PEG-400 as an inexpensive, easy to handle, non-toxic and recycl
- Sharma, Nutan,Sharma, Pankaj,Bhagat, Sunita
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p. 8721 - 8731
(2018/03/08)
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- Selective Hydrogenation of Nitriles to Primary Amines by using a Cobalt Phosphine Catalyst
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A general procedure for the catalytic hydrogenation of nitriles to primary amines by using a non-noble metal-based system is presented. Co(acac)3 in combination with tris[2-(dicyclohexylphosphino)ethyl]phosphine efficiently catalyzes the selective hydrogenation of a wide range of (hetero)aromatic and aliphatic nitriles to give the corresponding amines.
- Adam, Rosa,Bheeter, Charles Beromeo,Cabrero-Antonino, Jose R.,Junge, Kathrin,Jackstell, Ralf,Beller, Matthias
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p. 842 - 846
(2017/03/17)
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- Nitrile hydrogenation using nickel nanocatalysts in ionic liquids
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Ni nanoparticles (NPs) embedded in imidazolium based ionic liquids (ILs) have been proven to be versatile catalysts for the selective hydrogenation of benzonitrile to benzylamine with good recyclability in a biphasic system. Influence of the used ILs and reaction conditions has been examined in detail and a wider substrate scope has been studied using benzonitrile derivatives and aliphatic nitriles.
- Konnerth, Hannelore,Prechtl, Martin H. G.
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supporting information
p. 9594 - 9597
(2017/09/18)
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- NNP-Type Pincer Imidazolylphosphine Ruthenium Complexes: Efficient Base-Free Hydrogenation of Aromatic and Aliphatic Nitriles under Mild Conditions
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A series of seven novel NImNHP-type pincer imidazolylphosphine ruthenium complexes has been synthesized and fully characterized. The use of hydrogenation of benzonitrile as a benchmark test identified [RuHCl(CO)(NImNHPtBu)] as the most active catalyst. With its stable Ru-BH4 analogue, in which chloride is replaced by BH4, a broad range of (hetero)aromatic and aliphatic nitriles, including industrially interesting adiponitrile, has been hydrogenated under mild and base-free conditions.
- Adam, Rosa,Alberico, Elisabetta,Baumann, Wolfgang,Drexler, Hans-Joachim,Jackstell, Ralf,Junge, Henrik,Beller, Matthias
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p. 4991 - 5002
(2016/04/05)
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- Stable and Inert Cobalt Catalysts for Highly Selective and Practical Hydrogenation of C≡N and C=O Bonds
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Novel heterogeneous cobalt-based catalysts have been prepared by pyrolysis of cobalt complexes with nitrogen ligands on different inorganic supports. The activity and selectivity of the resulting materials in the hydrogenation of nitriles and carbonyl compounds is strongly influenced by the modification of the support and the nitrogen-containing ligand. The optimal catalyst system ([Co(OAc)2/Phenα-Al2O3]-800 = Cat. E) allows for efficient reduction of both aromatic and aliphatic nitriles including industrially relevant dinitriles to primary amines under mild conditions. The generality and practicability of this system is further demonstrated in the hydrogenation of diverse aliphatic, aromatic, and heterocyclic ketones as well as aldehydes, which are readily reduced to the corresponding alcohols.
- Chen, Feng,Topf, Christoph,Radnik, J?rg,Kreyenschulte, Carsten,Lund, Henrik,Schneider, Matthias,Surkus, Annette-Enrica,He, Lin,Junge, Kathrin,Beller, Matthias
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supporting information
p. 8781 - 8788
(2016/08/02)
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- Tuneable hydrogenation of nitriles into imines or amines with a ruthenium pincer complex under mild conditions
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The selective hydrogenation of aromatic and aliphatic nitriles into amines and imines is described. Using a ruthenium pincer complex, the selectivity towards amines or imines can be controlled by simple parameter changes. The reactions are conducted under very mild conditions between 50-100°C at 0.4 MPa H2 pressure without any additives at low catalytic loadings of 0.5-1 mol %, which results in quantitative conversions and high selectivity.
- Choi, Jong-Hoo,Prechtl, Martin H. G.
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p. 1023 - 1028
(2015/03/18)
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- Pyrrolidine(thi)ones Substituted by Heterocyclic Substituents in The 3-Position
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Pyrrolidine(thi)one compounds substituted by heterocyclic substituents in the 3-position, their preparation and use in pharmaceutical compositions, in particular as immunomodulators for treatment and/or inhibition of inflammatory and autoimmune diseases and haematological-oncological diseases.
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Page/Page column 16
(2009/01/20)
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- Syntheses, spectral, thermal and structural characterization of 2-phenyl-2-(1-hydroxyiminoethyl)-1,2,3,4-tetrahydroquinazoline and its novel nickel(II) complex
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The 2-phenyl-2-(1-hydroxyiminoethyl)-1,2,3,4-tetrahydroquinazoline (HL) and its NiII complex have been prepared and characterized by spectral method (FT-IR, NMR (13C and 1H), UV-vis.), elemental analysis, magnetic susceptibility and thermal analysis (TG, DTA) techniques. The crystal structures of HL and NiII complex were also determined by the single crystal X-ray diffraction. The HL and NiII complex crystallizes in the monoclinic and triclinic, space groups P21/c and P1, respectively. The complex was occurred by the elimination of 1 mole of 2-aminobenzylamine from the 2 moles of the HL after the ring opening reaction by the NiII attack. Crystallographic study reveal that Ni II atom has a square planer geometry being coordinated by four nitrogen atoms of HL. Two thermal processes of the HL and NiII complex can occur in TG and DTA curves.
- Colak, Alper Tolga,Tas, Murat,Irez, Gazi,Yesilel, Okan Zafer,Bueyuekguengoer, Orhan
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p. 504 - 508
(2008/10/09)
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- SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS
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The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed
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- Synthesis and antimicrobial activity of N-(substitutedphenyl)-N'-[1,2,3,4-tetrahydro-2-oxido- 1,3,2-benzodiazaphosphorine-2-y1] ureas
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N-(Substitutedphenyl)-N′-[1,2,3,4-tetrahydro-2-oxido- 1,3,2-benzodiazaphosphorine-2-y1] ureas 5 which are substituted ureas of the type RR′P(O)NHC(O)NR″R? have been synthesized from reactions of 2-aminobenzylamine 2 with chlorides of arylcarbamidophosphor
- Nagaprasada Rao,Reddy,Reddy
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p. 817 - 821
(2007/10/03)
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- Process for the preparation of toluylene diisocyanate, specific mixtures of toluylene diamine and water, and the use of toluylene diamine and water mixtures to prepare toluylene diisocyanate
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Toluylene diisocyanate is produced by nitration of toluene toy yield dinitrotoluene, hydrogenation of the dinitrotoluene, optionally in the presence of a solvent or diluent, to yield a crude solution of toluylene diamine and reaction water, processing the crude solution of toluylene diamine and water to yield an intermediate mixture of toluylene diamine and water wherein the processing is interrupted to result in a water content of about 1-40% by weight, preferably about 2-10% by weight of the intermediate mixture, transporting this intermediate mixture from a first production facility to a second production facility, whereat the intermediate mixture of TDA and water is completed to yield dry toluylene diamine of commercial quality, and followed by phosgenation of the toluylene diamine to give toluylene diisocyanate. It is optional to additionally process the dry toluylene diamine prior to phosgenation. The invention also relates to intermediate mixtures of toluylene diamine and water which have a solidification point of at most 95° C., and the use of these intermediate mixtures for producing toluylene diisocyanate. It is preferable that the use of these intermediate mixtures to produce toluylene diisocyanate is performed at a site (or location) which is different from the site of production of the intermediate mixtures of toluylene diamine and water.
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- Process for the preparation of chlorine-substituted aromatic amines and of catalysts
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Chlorine-substituted aromatic amines are prepared by the hydrogenation of chlorine-substituted aromatic nitro compounds in the presence of a catalyst containing platinum and nickel and/or cobalt on an activated charcoal support, the platinum having been simultaneously deposited and reduced on the activated charcoal support in the preparation of the catalyst. Such catalysts are furthermore prepared, as are catalysts containing noble metals on an activated charcoal support, it also being possible for the latter to be used for the reduction of nitronaphthalenes or nitrotoluenes.
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- Synthesis of 3,1-benzoxazines and tetrahydroquinazolines from o-aminobenzyl alcohol and o-aminobenzyl amine - Semi-empirical MO calculations
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o-Aminobenzyl alcohol (4) reacts with aldehydes and ketones to the 3,1-benzoxazines 20a/b and 22a/b, whereas the enamine derivatives 24a-c are formed from β-diketones. The isosteric o-amino-benzylamine (1) gives tetrahydroquinazolines 11a/b and 14b as het
- Lessel
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p. 329 - 336
(2007/10/02)
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- Technetium-99m N,N'-Bis(2-mercapto-2-methylpropyl)-2-aminobenzylamine: Technetium-99m Complexes of a Novel Bis(aminoethanethiol) Ligand
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A new N2S2 ligand system, N,N'-bis(2-mercapto-2-methylpropyl)-2-aminobenzylamine, U-BAT, 1, containing uneven amine groups (two amine groups with different pKa values) for complexing VO>3+, was prepared.The reaction of this novel ligand with pertechnetate, in the presence of stannous tartrate as the reducting agent, produces the neutral and lipid-soluble TcVO(U-BAT), TcS2C15H23N2O, 2.However, when the same reaction was carried out at a higher pH, 9-10, and with 30 min of heating (100 deg C), a second neutral but more lipid-soluble complex, TcVO(OU-BAT), TcS2C15H21N2O, 3, was isolated.The X-ray crystallography data of the 99Tc complexes show square pyramidal coordination with N2S2 as the base and the Tc=O in the apical position.Compound 3 can be derived from 2 by an oxidation of the ligand to form an imine.After iv injection into rats, the neutral and lipid-soluble technetium-99m complexes showed significant brain uptake, 1.54 and 1.07percent dose/organ at 2 min for TcVO(U-BAT) and TcVO(OU-BAT), respectively.The novel Tc chemistry of this new ligand system may provide a useful foundation for designing Tc complexes with a built-in redox mechanism.
- Francesconi, Lynn C.,Yang, Yun Y.,Kung, Mei-Ping,Zhang, Xiao X.,Billings, Jeffrey J.,et al.
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p. 3282 - 3288
(2007/10/02)
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- Process for producing aminobenzylamines
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Aminobenzylamines are produced by catalytically reducing o-, m- or p-nitrobenzaldoxime in an organic solvent in the presence of a compound selected from the group consisting of (a) boric acid, phosphoric acid and/or anhydrides thereof, (b) CO2 gas and (c) an organic acid. The starting material, nitrobenzaldoxime is produced by reaction of the corresponding nitrobenzaldehyde with hydroxylamine.
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- Synthesis and immunomodulating activity of 5H-thiazolo[2,3-b]quinazolin-3(2H)-one
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The synthesis and immunomodulating activity of 5H-thiazolo[2,3-b]quinazolin-3(2H)-one (7) are described. When tested in the Kennedy plaque assay, 7 exerted immunosuppressive activity on IgM production in female C3H mice sensitized with sheep erythrocytes.
- Bennett,Radov,Trusso,Georgiev St.
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p. 633 - 634
(2007/10/02)
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- Synthesis of 2-Substituted Quinazolines and Quinazolones as Potential Anthelmintics
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2-Substituted quinazolines (5, 6) and quinazolones (9-18) have been synthesized starting from 2-aminobenzylamine (3) and 2-carbethoxyquinazolone (7), respectively.The compounds have been tested for their antihookworm activity against Ancylostoma ceylanicum in hamsters but none shows any significant activity.
- Rastogi, Rashmi,Sharma, Satyavan
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p. 744 - 746
(2007/10/02)
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- Synthesis and Adrenergic Blocking Effects of 2-(Alkylamino)-3,4-dihydroquinazolines
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Based on the known biological activity of a variety of guanidine-containing agents, several N-substituted 3,4-dihydroquinazolines were synthesized.These compounds can be considered to be rigid analogues of phenylguanidines.In anesthetized rats the compounds decreased blood pressure and were antagonist of the pressor response to norepinephrine.
- Grosso, John A.,Nichols, David E.,Nichols, Maxine B.,Yim, George K. W.
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p. 1261 - 1264
(2007/10/02)
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- Method for preparing aromatic urethans
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In the preparation of aromatic urethans, a dialkyl carbonate is reacted with an N-acyl derivative of an amine: thus, for example, by reacting acetanilide with a lower dialkyl carbonate, such as DMC or DEC, in the presence of titanium tetraphenate (Lewis' acid), phenylmethyl urethan is obtained with a yield over 90%. No toxic reactants are used and the reaction has outstandingly high yields and conversion ratings. The urethane in question are useful as weed-killers and pesticides in agriculture.
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