- Green and convenient protocols for the efficient reduction of nitriles and nitro compounds to corresponding amines with NaBH4 in water catalyzed by magnetically retrievable CuFe2O4 nanoparticles
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Abstract: In this study, firstly, CuFe2O4 nanoparticles were prepared by a simple operation. The structure of the mentioned nanoparticles was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma-optical emission spectrometry, vibrating sample magnetometer and also Brunauer–Emmett–Teller and Barrett–Joyner–Halenda analyses. The prepared magnetically copper ferrite nanocomposite was successfully applied as a simple, cost-effective, practicable, and recoverable catalyst on the green, highly efficient, fast, base-free, and ligand-free reduction of nitriles and also on the affordable and eco-friendly reduction of nitro compounds with the broad substrate scope to the corresponding amines with NaBH4 in water at reflux in high to excellent yields. Graphical abstract: [Figure not available: see fulltext.].
- Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh,Mousavi, Hossein
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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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- Mild palladium-catalysed highly efficient hydrogenation of CN, C-NO2, and CO bonds using H2 of 1 atm in H2O
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Here we present the first example of a mild and high-efficiency protocol enabling a process in water using 1 atm of H2 for the efficient and selective hydrogenation of nitriles, nitro compounds, ketones, and aldehydes to yield primary amines and alcohols with satisfactory yields of up to >99%. Several palladium-based nanoparticle catalysts were prepared from K2PdCl4 and ligands, and one of them was found to be the best and most suitable for the hydrogenation of CN, C-NO2, and CO bonds. In addition, the catalyst Pd-NPs can be easily recycled and reused without losing their activity and selectivity. A plausible mechanism for the hydrogenation of a CN bond was also proposed, representing the first example that possesses great potential for sustainable industrial purposes.
- Liu, Yaxu,He, Shaopo,Quan, Ziyi,Cai, Huizhuo,Zhao, Yang,Wang, Bo
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supporting information
p. 830 - 838
(2019/02/27)
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- A ppm level Rh-based composite as an ecofriendly catalyst for transfer hydrogenation of nitriles: Triple guarantee of selectivity for primary amines
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Hydrogenation of nitriles to afford amines under mild conditions is a challenging task with an inexpensive heterogeneous catalyst, and it is even more difficult to obtain primary amines selectively because of the accompanying self-coupling side reactions. An efficient catalytic system was designed as Fe3O4@nSiO2-NH2-RhCu@mSiO2 to prepare primary amines through the transfer hydrogenation of nitrile compounds with economical HCOOH as the hydrogen donor. The loading of rhodium in the catalyst could be at the ppm level, and the TOF reaches 6803 h-1 for Rh. This catalytic system has a wide substrate range including some nitriles that could not proceed in the previous literature. The experimental results demonstrate that the excellent selectivity for primary amines is guaranteed by three tactics, which are the strong active site, the inhibition of side products by the hydrogen source and the special pore structure of the catalyst. In addition, the catalyst could be reused ten times without activity loss through convenient magnetic recovery.
- Liu, Lei,Li, Jifan,Ai, Yongjian,Liu, Yuhong,Xiong, Jialiang,Wang, Hongdong,Qiao, Yijun,Liu, Wenrui,Tan, Shanchao,Feng, Shaofei,Wang, Kunpeng,Sun, Hongbin,Liang, Qionglin
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p. 1390 - 1395
(2019/03/26)
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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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- Cobalt-Catalyzed and Lewis Acid-Assisted Nitrile Hydrogenation to Primary Amines: A Combined Effort
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The selective hydrogenation of nitriles to primary amines using a bench-stable cobalt precatalyst under 4 atm of H2 is reported herein. The catalyst precursor was reduced in situ using NaHBEt3, and the resulting Lewis acid formed, BEt3, was found to be integral to the observed catalysis. Mechanistic insights gleaned from para-hydrogen induced polarization (PHIP) transfer NMR studies revealed that the pairwise hydrogenation of nitriles proceeded through a Co(I/III) redox process.
- Tokmic, Kenan,Jackson, Bailey J.,Salazar, Andrea,Woods, Toby J.,Fout, Alison R.
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supporting information
p. 13554 - 13561
(2017/10/05)
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- Small Molecule Inhibitors Simultaneously Targeting Cancer Metabolism and Epigenetics: Discovery of Novel Nicotinamide Phosphoribosyltransferase (NAMPT) and Histone Deacetylase (HDAC) Dual Inhibitors
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Cancer metabolism and epigenetics are among the most intensely pursued research areas in anticancer drug discovery. Here we report the first small molecules that simultaneously inhibit nicotinamide phosphoribosyltransferase (NAMPT) and histone deacetylase (HDAC), two important targets of cancer metabolism and epigenetics, respectively. Through iterative structure-based drug design, chemical synthesis, and biological assays, a highly potent dual NAMPT and HDAC inhibitor was successfully identified. Compound 35 possessed excellent and balanced activities against both NAMPT (IC50 = 31 nM) and HDAC1 (IC50 = 55 nM). It could effectively induce cell apoptosis and autophagy and ultimately led to cell death. Importantly, compound 35 showed excellent in vivo antitumor efficacy in the HCT116 xenograft model. This proof-of-concept study demonstrates the feasibility of discovering an inhibitor targeting cancer metabolism and epigenetics and provides an efficient strategy for multitarget antitumor drug discovery.
- Dong, Guoqiang,Chen, Wei,Wang, Xia,Yang, Xinglin,Xu, Tianying,Wang, Pei,Zhang, Wannian,Rao, Yu,Miao, Chaoyu,Sheng, Chunquan
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p. 7965 - 7983
(2017/10/18)
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- A rapid and practical protocol for solvent-free reduction of oximes to amines with NaBH4/ZrCl4/Al2O3 system
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Solvent-free reduction of various aldoximes and ketoximes to the corresponding amines was performed easily and efficiently with NaBH4 in the presence of ZrCl4 supported on Al2O3. The reactions were carried out rapidly (within 2 min) at room temperature to afford the amines in high to excellent yields.
- Zeynizadeh, Behzad,Kouhkan, Mehri
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experimental part
p. 3448 - 3452
(2012/02/01)
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- Synthesis of potent and selective 2-azepanone inhibitors of human tryptase
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The serine protease tryptase has been associated with a broad range of allergic and inflammatory diseases and, in particular, has been implicated as a critical mediator of asthma. The inhibition of tryptase therefore has the potential to be a valuable therapy for asthma. The synthesis, employing solution phase parallel methods, and SAR of a series of novel 2-azepanone tryptase inhibitors are presented. A member of this series, 8t, was identified as a potent inhibitor of human tryptase (IC50=38 nM) with selectivity ≤330-fold versus related serine proteases (trypsin, plasmin, uPA, tPA, APC, alpha-thrombin, and FXa).
- Zhao, Guohua,Bolton, Scott A.,Kwon, Chet,Hartl, Karen S.,Seiler, Steven M.,Slusarchyk, William A.,Sutton, James C.,Bisacchi, Gregory S.
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p. 309 - 312
(2007/10/03)
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- Amide and diamide inhibitors of IMPDH enzyme for use in treating IMPDH-associated disorders
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The present invention discloses the identification of the inhibitors of IMPDH (inosine-5′-monophosphate dehydrogenase). The compounds and pharmaceutical compositions disclosed herein are useful in treating or preventing IMPDH associated disorders, such as transplant rejection and autoimmune diseases.
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- Novel thiourea derivatives and the pharmaceutical compositions containing the same
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The present invention relates to novel thiourca derivatives as a modulator for vanilloid receptor (VR) and the phar- maceutical compositions containing the same. As diseases associated with the activity of vanilloid receptor, pain acute pain, chronic pain, neuropathic pain, post-operative pain, migraine, arthralgia, neuropathies, nerve injury, diabetic neuropathy, neurodegeneration, neurotic skin disorder, stroke, urinary bladder hypersensitiveness, irritable bowel syndrome, a respiratory disorder such as asthma or chronic obstructive pulmonary disease, irritation of skin, eye or mucous membrane, fervescence, stomach-duodenal ulcer, inflam- matory bowel disease and inflammatory diseases can be enumerated. The present invention provides a pharmaceutical composition for prevention or treatment of these diseases.
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- Novel diamide-based inhibitors of IMPDH
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A series of novel amide-based small molecule inhibitors of inosine monophosphate dehydrogenase is described. The synthesis and the structure-activity relationships (SARs) derived from in vitro studies are presented.
- Gu, Henry H.,Iwanowicz, Edwin J.,Guo, Junqing,Watterson, Scott H.,Shen, Zhongqi,Pitts, William J.,Dhar,Fleener, Catherine A.,Rouleau, Katherine,Sherbina,Witmer, Mark,Tredup, Jeffrey,Hollenbaugh, Diane
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p. 1323 - 1326
(2007/10/03)
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- Inhibitors of IMPDH enzyme
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The present invention discloses the identification of the novel inhibitors of IMPDH (inosine-5′-monophosphate dehydrogenase). The compounds and pharmaceutical compositions disclosed herein are useful in treating or preventing IMPDH-associated disorders, such as transplant rejection and autoimmune diseases.
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- Indium Mediated Reduction of Nitro and Azide Groups in the Presence of HCl in Aqueous Media
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Indium mediated reduction of azide and nitro groups in the presence of HCl (1.5 equiv based on indium) at room temperature in aqueous THF successfully provided the corresponding amine in high to quantitative yields. Under the some reaction conditions, selective reduction of azide and nitro group in the presence of vinyl group could be accomplished.
- Lee, Jung Gyu,Choi, Kyung Il,Koh, Hun Yeong,Kim, Youseung,Kang, Yonghan,Cho, Yong Seo
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- Acetamidine derivatives and their use as inhibitors for the nitric oxide synthase
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A class of acetamidine derivatives of general formula (I) STR1 wherein R1 is hydrogen, C1-6 hydrocarbyl group optionally substituted by halo, halo, nitro, cyano or a group XR3 wherein X is oxygen, C(O)m wherein m is 1 or 2, S(O)n wherein n is 0, 1 or 2, or a group NR4 wherein R4 is hydrogen or C1-6 alkyl; and R3 is hydrogen, C1-6 alkyl, or a group NR5 R6 wherein R5 and R6 are independently hydrogen or C1-6 alkyl, provided that R3 is not NR5 R6 when X is oxygen or S(O)n; R1a and R1b are independently selected from hydrogen and halo; R2 is a C1-14 hydrocarbyl group which may optionally contain one or two heteroatoms, the group R2 being optionally substituted by one or more groups independently selected from halo; N3 ; nitro; CF3 ; ZR7 wherein Z is oxygen, C(O)m' wherein m' is 1 or 2, S(O)n' wherein n' is 0, 1 or 2, or a group NR8 wherein R8 is hydrogen or C1-6 alkyl and R7 is hydrogen, C1-6 alkyl or a group NR9 R10 wherein R9 and R10 are independently hydrogen or C1-6 alkyl; or R2 is substituted by a group (a) STR2 wherein R11 has a definition the same as for R1 ; with the proviso that when R1 is a C1-6 alkyl group and R2 is a C1-14 hydrocarbyl substituted by two groups ZR7 wherein one group ZR7 is CO2 H, the other group ZR7 is not NH2; and salts thereof, methods for the manufacture thereof, and therapies, particularly inhibtion of nitric oxide synthase, is disclosed.
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- N-phenylamidines as selective inhibitors of human neuronal nitric oxide synthase: Structure-activity studies and demonstration of in vivo activity
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Selective inhibition of the neuronal isoform of nitric oxide synthase (NOS) compared to the endothelial and inducible isoforms may be required for treatment of neurological disorders caused by excessive production of nitric oxide. Recently, we described N-(3-(aminomethyl)benzyl)acetamidine (13) as a slow, tight-binding inhibitor, highly selective for human inducible nitric oxide synthase (iNOS). Removal of a single methylene bridge between the amidine nitrogen and phenyl ring to give N-(3- (aminomethyl)phenyl)acetamidine (14) dramatically altered the selectivity to give a neuronal selective nitric oxide synthase (nNOS) inhibitor. Part of this large shift in selectivity was due to 14 being a rapidly reversible inhibitor of iNOS in contrast to the essentially irreversible inhibition of iNOS observed with 13. Structure-activity studies revealed that a basic amine functionality tethered to an aromatic ring and a sterically compact amidine are key pharmacophores for this class of NOS inhibitors. Maximal nNOS inhibition potency was achieved with N-(3-(aminomethyl)phenyl)-2- furanylamidine (77) (K(i-nNOS) = 0.006 μM; K(i-eNOS) = 0.35 μM; K(i-iNOS) = 0.16 μM). Finally, α-fluoro-N-(3-(aminomethyl)phenyl)acetamidine (74) (K(i- nNOS) = 0.011 μM; K(i-eNOS) = 1.1 μM; K(i-iNOS) = 0.48 μM) had excellent brain penetration and inhibited nNOS in a rat brain slice assay as well as in the rat brain (cerebellum) in vivo. Thus, N-phenylamidines should be useful in validating the role of nNOS in neurological disorders.
- Collins, Jon L.,Shearer, Barry G.,Oplinger, Jeffrey A.,Lee, Shuliang,Garvey, Edward P.,Salter, Mark,Duffy, Claire,Burnette, Thimysta C.,Furfine, Eric S.
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p. 2858 - 2871
(2007/10/03)
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- Preparation of nucleoside uronamides as A3 adenosine receptor agonists.
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The present invention provides N 6-benzyladenosine-5'-N-uronamide and related substituted compounds, particularly those containing substituents on the benzyl and/or uronamide groups, and modified xanthine ribosides, as well as pharmaceutical compositions containing such compounds. The present invention also provides a method of selectively activating an A 3 adenosine receptor in a mammal, which method comprises acutely or chronically administering to a mammal in need of selective activation of its A 3 adenosine receptor a therapeutically effective amount of a compound which binds with the A. sub.3 receptor so as to stimulate an A 3 receptor-dependent response.
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- The reduction of aromatic oximes to amines with borohydride exchange resin-nickel acetate system
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Aromatic oximes were reduced to the corresponding amines with borohydride supported on an ion exchange resin (BER)- nickel acetate in methanol in good yields. The isolation of pure products by simple filtration and evaporation is an important feature of this method.
- Bandgar,Nikat,Wadgaonkar
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p. 863 - 869
(2007/10/02)
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- Process for producing aminobenzylamine
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A commercially advantageous process for producing m- or p-aminobenzylamine is provided, which is characterized by subjecting m- or p-nitrobenzaldehyde and ammonia to catalytic reduction in the presence of a reducing catalyst in an organic solvent; in the reduction, when nitrobenzaldehyde and ammonia are in advance made a mixed solution in an organic solvent, and this solution is added in divided manner, the yield being further improved.
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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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- Aminobenzylamine composition
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A composition of aminobenzylamine is provided which is mainly composed of m-aminobenzylamine and p-aminobenzylamine in either the presence or absence of a small quantity of o-aminobenzylamine, is liquid at room temperature, and is an excellent cold-setting type curing agent useful for thermosetting resin compositions.
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- Novel monoazo and disazo colorants from aminoalkylanilines and bis(aminoalkyl)anilines
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Water-insoluble azo dyestuffs of the formula STR1 and water-soluble acid addition salts thereof useful for coloring natural fibers, synthetic fiber-forming material and cellulosic materials as well as in the manufacture of paper, varnishes, inks, coatings and plastics in which A represents an azoic coupling radical derived from a coupling component selected from the group consisting of arylides of hydroxy-substituted carbocyclic aromatic carboxylic acids, 1-aryl-5-hydroxy-pyrazoles, 6-amino-1-naphthol-3-sulfonic acid, and compounds having an enolizable ketomethylene group of the formula STR2 R is hydrogen, lower-alkyl, lower-alkoxy or halogen; R2 is hydrogen, lower-alkyl, lower-alkoxy, halogen, aminomethyl or 2-aminoethyl with the proviso that A is other than β-naphthol when R2 is aminomethyl or 2-aminoethyl; R1 and R3 are the same or different and are each hydrogen, lower-alkyl, lower-alkoxy, halogen or aminomethyl with the proviso that at least one of R1 and R3 is aminomethyl when R2 is other than aminomethyl or 2-aminoethyl; and n represents an integer whose value is 1 or 2 and corresponds to the number of azo linkages, which dyestuffs are obtained by coupling a diazotized amine of the formula STR3 in which R, R1, R2 and R3 are as defined above with said coupling component.
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- Monoazo and diazo colorants from aminoalkylanilines and bis(aminoalkyl)anilines
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Water-insoluble azo dyestuffs of the formula STR1 AND WATER-SOLUBLE ACID ADDITION SALTS THEREOF USEFUL FOR COLORING NATURAL FIBERS, SYNTHETIC FIBER-FORMING MATERIAL AND CELLULOSIC MATERIALS AS WELL AS IN THE MANUFACTURE OF PAPER, VARNISHES, INKS, COATINGS AND PLASTICS IN WHICH A represents an azoic coupling radical derived from a coupling component selected from the group consisting of arylides of hydroxysubstituted carbocyclic aromatic carboxylic acids, 1-aryl-5-hydroxypyrazoles, 6-amino-1-naphthol-3-sulfonic acid, and compounds having an enolizable ketomethylene group of the formula STR2 R is hydrogen, lower-alkyl, lower-alkoxy or halogen; R2 is hydrogen, lower-alkyl, lower-alkoxy, halogen, aminomethyl or 2-aminoethyl with the proviso that A is other than β-naphthol when R2 is aminomethyl or 2-aminoethyl; R1 and R3 are the same or different and are each hydrogen, lower-alkyl, lower-alkoxy, halogen or aminomethyl with the proviso that at least one of R1 and R3 is aminomethyl when R2 is other than aminomethyl or 2-aminoethyl; and n represents an integer whose value is 1 or 2 and corresponds to the number of azo linkages, which dyestuffs are obtained by coupling a diazotized amine of the formula STR3 in which R, R1, R2 and R3 are as defined above with said coupling component.
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