- Citric acid catalysed Beckmann rearrangement, under solvent free conditions
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Citric acid is reported to be a highly efficient and eco-friendly catalyst for the Beckmann rearrangement under solvent free conditions.
- Thopate, Shankar Ramchandra,Kote, Santosh Rajaram,Rohokale, Sandeep Vasantrao,Thorat, Nitin Madhukar
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Read Online
- In situ generated iron oxide nanocrystals as efficient and selective catalysts for the reduction of nitroarenes using a continuous flow method
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The best of both worlds: The benefits of homogeneous and heterogeneous nanocatalysis are combined, whereby highly reactive colloidal Fe 3O4 nanocrystals are generated in situ that remain in solution long enough to allow the efficient and selective reduction of nitroarenes to anilines in continuous-flow mode (see scheme). After completion of the reaction, the nanoparticles aggregate and can be recovered by a magnet. Copyright
- Cantillo, David,Baghbanzadeh, Mostafa,Kappe, C. Oliver
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Read Online
- Radical arylation of triphenyl phosphite catalyzed by salicylic acid: Mechanistic investigations and synthetic applications
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A straightforward and scalable methodology to synthesize diphenyl arylphosphonates at 20 °C within 1-2 h is reported using inexpensive SA as the catalytic promoter of the reaction. Mechanistic investigations suggest that the reaction proceeds via radical-radical coupling, consistent with the so-called persistent radical effect. The reaction tolerated a wide range of functional groups and heteroaromatic moieties. The synthetic usefulness and the unique reactivity of the obtained phosphonates were demonstrated in different one-step transformations.
- Estruch-Blasco, Manel,Felipe-Blanco, Diego,Bosque, Irene,Gonzalez-Gomez, Jose C.
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Read Online
- Copper nanoparticles (CuNPs) catalyzed chemoselective reduction of nitroarenes in aqueous medium
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Abstract: A procedure for practical synthesis of CuNPs from CuSO4·5H2O is established, under appropriate reaction conditions, using rice (Oryza sativa) as an economic source of reducing as well as a stabilizing agent. Optical and microscopic techniques are employed for the characterization of the synthesized CuNPs and the sizes of the particles were found to be in the range of 8 ± 2 nm. The nanoparticles are used as a catalyst for chemoselective reduction of aromatic nitro compounds to corresponding amines under ambient conditions and water as a reaction medium. Graphic abstract: CuNPs are synthesized using hydrolysed rice and used as catalyst for chemoselective reduction of nitroarenes to their corresponding amines in water. [Figure not available: see fulltext.]
- Chand, Dillip Kumar,Rai, Randhir
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- Preparation method of aminoacetanilide
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The invention belongs to the technical field of dye intermediate production, and particularly relates to a preparation method of aminoacetanilide, which comprises the following steps of 1) adding an acetate compound, phenylenediamine and a catalyst triethylene diamine into a reactor, and uniformly mixing to obtain a mixed solution, 2) under the protection of nitrogen, heating the mixed solution to65-90 DEG C, dropwise adding acetic acid, and reacting for 4-9 hours after dropwise adding is finished, and 3) after the reaction is finished, cooling to 15-25 DEG C, standing for 5-8 hours, filtering, fully washing a filter cake with n-butyl alcohol, and drying in vacuum at 80 DEG C for 6 hours to obtain aminoacetanilide. Aminoacetanilide is synthesized by using an acetate method, acetic anhydride which is high in price and easy to prepare drugs is not used, the production cost is reduced, and the method is suitable for industrial production; the method has the advantages of few reaction steps, no generation of waste acid, waste water and waste salt and no pollution to the environment; the yield (based on the weight of phenylenediamine) of the aminoacetanilide product prepared by the method is up to 97% or above, and the purity is up to 98% or above.
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Paragraph 0046-0064
(2021/01/29)
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- Applicability of aluminum amalgam to the reduction of arylnitro groups
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An array of arylnitro compounds with various functionality were treated with freshly-prepared aluminum amalgam in THF/water solution and resulted in the corresponding arylamines. The Al(Hg)-mediated reductions are relatively rapid with consumption of the amalgam and disappearance of starting material occurring over 20–30 min. The workup of the reductions involves only removal of the insoluble by-products by filtration followed by concentration. Only in some cases is chromatography required to secure the pure product. The desired arylamines are furnished in quantities of 25–100 mg, which in some cases, could be taken on to the next reaction without further purification. Reductions of 4-nitrobenzyl derivatives of carbohydrates or nucleosides were selective in affording the corresponding 4-aminobenzyl products. To show applicability in click chemistry, selected aminobenzyl products are directly azidated to yield products that were then used in click reactions to afford the corresponding 1,2,3-triazoles.
- Luzzio, Frederick A.,Monsen, Paige J.
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supporting information
(2020/11/02)
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- 2-Arylamino-6-ethynylpurines are cysteine-targeting irreversible inhibitors of Nek2 kinase
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Renewed interest in covalent inhibitors of enzymes implicated in disease states has afforded several agents targeted at protein kinases of relevance to cancers. We now report the design, synthesis and biological evaluation of 6-ethynylpurines that act as covalent inhibitors of Nek2 by capturing a cysteine residue (Cys22) close to the catalytic domain of this protein kinase. Examination of the crystal structure of the non-covalent inhibitor 3-((6-cyclohexylmethoxy-7H-purin-2-yl)amino)benzamide in complex with Nek2 indicated that replacing the alkoxy with an ethynyl group places the terminus of the alkyne close to Cys22 and in a position compatible with the stereoelectronic requirements of a Michael addition. A series of 6-ethynylpurines was prepared and a structure activity relationship (SAR) established for inhibition of Nek2. 6-Ethynyl-N-phenyl-7H-purin-2-amine [IC50 0.15 μM (Nek2)] and 4-((6-ethynyl-7H-purin-2-yl)amino)benzenesulfonamide (IC50 0.14 μM) were selected for determination of the mode of inhibition of Nek2, which was shown to be time-dependent, not reversed by addition of ATP and negated by site directed mutagenesis of Cys22 to alanine. Replacement of the ethynyl group by ethyl or cyano abrogated activity. Variation of substituents on the N-phenyl moiety for 6-ethynylpurines gave further SAR data for Nek2 inhibition. The data showed little correlation of activity with the nature of the substituent, indicating that after sufficient initial competitive binding to Nek2 subsequent covalent modification of Cys22 occurs in all cases. A typical activity profile was that for 2-(3-((6-ethynyl-9H-purin-2-yl)amino)phenyl)acetamide [IC50 0.06 μM (Nek2); GI50 (SKBR3) 2.2 μM] which exhibited >5-10-fold selectivity for Nek2 over other kinases; it also showed > 50% growth inhibition at 10 μM concentration against selected breast and leukaemia cell lines. X-ray crystallographic analysis confirmed that binding of the compound to the Nek2 ATP-binding site resulted in covalent modification of Cys22. Further studies confirmed that 2-(3-((6-ethynyl-9H-purin-2-yl)amino)phenyl)acetamide has the attributes of a drug-like compound with good aqueous solubility, no inhibition of hERG at 25 μM and a good stability profile in human liver microsomes. It is concluded that 6-ethynylpurines are promising agents for cancer treatment by virtue of their selective inhibition of Nek2. This journal is
- Bayliss, Richard,Boxall, Kathy,Carbain, Benoit,Coxon, Christopher R.,Fry, Andrew M.,Golding, Bernard T.,Griffin, Roger J.,Hardcastle, Ian R.,Harnor, Suzannah J.,Mas-Droux, Corine,Matheson, Christopher J.,Newell, David R.,Richards, Mark W.,Sivaprakasam, Mangaleswaran,Turner, David,Cano, Céline
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supporting information
p. 707 - 731
(2020/08/24)
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- Probing 2H-Indazoles as Templates for SGK1, Tie2, and SRC Kinase Inhibitors
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The broader and systematic application of a novel scaffold is often hampered by the unavailability of a short and reliable synthetic access. We investigated a new strategy for the design and synthesis of an array of N2-substituted aza-2H-indazole derivatives as potential kinase inhibitors. Guided by a rational ligand alignment approach to qualify the so-far underrepresented aza-2H-indazole scaffold, indazoles were connected at the N2 position with a phenyl spacer and an arylsulfonamide or amide linkage. Initial profiling against a panel of 30 kinases confirmed the in silico predicted selectivity bias. A synthesized focused library of 52 different aza-2H-indazole derivatives showed good initial selective inhibition against SGK1, Tie2, and SRC kinases, with the best representatives having IC50 values in the range of 500 nm. In a comparative computational study, these data were analyzed and rationalized in light of docking studies.
- Schoene, Jens,Gazzi, Thais,Lindemann, Peter,Christmann, Mathias,Volkamer, Andrea,Nazaré, Marc
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p. 1514 - 1527
(2019/08/07)
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- Synergistic effects in Fe nanoparticles doped with ppm levels of (Pd + Ni). A new catalyst for sustainable nitro group reductions
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A remarkable synergistic effect has been uncovered between ppm levels of Pd and Ni embedded within iron nanoparticles that leads to mild and selective catalytic reductions of nitro-containing aromatics and heteroaromatics in water at room temperature. NaBH4 serves as the source of inexpensive hydride. Broad substrate scope is documented, along with several other features including: low catalyst loading, low residual metal in the products, and recycling of the catalyst and reaction medium, highlight the green nature of this new technology.
- Pang, Haobo,Gallou, Fabrice,Sohn, Hyuntae,Camacho-Bunquin, Jeffrey,Delferro, Massimiliano,Lipshutz, Bruce H.
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supporting information
p. 130 - 135
(2018/01/12)
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- Potent and Selective Inhibitors of 8-Oxoguanine DNA Glycosylase
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The activity of DNA repair enzyme 8-oxoguanine DNA glycosylase (OGG1), which excises oxidized base 8-oxoguanine (8-OG) from DNA, is closely linked to mutagenesis, genotoxicity, cancer, and inflammation. To test the roles of OGG1-mediated repair in these pathways, we have undertaken the development of noncovalent small-molecule inhibitors of the enzyme. Screening of a PubChem-annotated library using a recently developed fluorogenic 8-OG excision assay resulted in multiple validated hit structures, including selected lead hit tetrahydroquinoline 1 (IC50 = 1.7 μM). Optimization of the tetrahydroquinoline scaffold over five regions of the structure ultimately yielded amidobiphenyl compound 41 (SU0268; IC50 = 0.059 μM). SU0268 was confirmed by surface plasmon resonance studies to bind the enzyme both in the absence and in the presence of DNA. The compound SU0268 was shown to be selective for inhibiting OGG1 over multiple repair enzymes, including other base excision repair enzymes, and displayed no toxicity in two human cell lines at 10 μM. Finally, experiments confirm the ability of SU0268 to inhibit OGG1 in HeLa cells, resulting in an increase in accumulation of 8-OG in DNA. The results suggest the compound SU0268 as a potentially useful tool in studies of the role of OGG1 in multiple disease-related pathways.
- Tahara, Yu-Ki,Auld, Douglas,Ji, Debin,Beharry, Andrew A.,Kietrys, Anna M.,Wilson, David L.,Jimenez, Marta,King, Daniel,Nguyen, Zachary,Kool, Eric T.
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supporting information
p. 2105 - 2114
(2018/02/19)
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- Synthesis and in-vitro evaluation of 2-amino-4-arylthiazole as inhibitor of 3D polymerase against foot-and-mouth disease (FMD)
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Foot-and-mouth disease (FMD) is a highly contagious vesicular disease of livestock caused by a highly variable RNA virus, foot-and-mouth disease virus (FMDV). One of the targets to suppress expansion of and to control FMD is 3D polymerase (FMDV 3Dpol). In this study, 2-amino-4-arylthiazole derivatives were synthesized and evaluated for their inhibitory activity against FMDV 3Dpol. Among them, compound 20i exhibited the most potent functional inhibition (IC50 = 0.39μM) of FMDV 3D polymerase and compound 24a (EC50=13.09 μM) showed more potent antiviral activity than ribavirin (EC50=1367 μM) and T1105 (EC50=347 μM) with IBRS-2 cells infected by the FMDV O/SKR/2010 strain.
- Jeong, Kwi-Wan,Lee, Jung-Hun,Park, Sun-Mi,Choi, Joo-Hyung,Jeong, Dae-Youn,Choi, Dong-Hwa,Nam, Yeonju,Park, Jong-Hyeon,Lee, Kwang-Nyeong,Kim, Su-Mi,Ku, Jin-Mo
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p. 387 - 397
(2015/09/01)
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- Novel trisubstituted acridines as human telomeric quadruplex binding ligands
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A novel series of trisubstituted acridines were synthesized with the aim of mimicking the effects of BRACO19. These compounds were synthesized by modifying the molecular structure of BRACO19 at positions 3 and 6 with heteroacyclic moieties. All of the derivatives presented in the study exhibited stabilizing effects on the human telomeric DNA quadruplex. UV-vis spectroscopy, circular dichroism, linear dichroism and viscosimetry were used in order to study the nature of the DNA binding in more detail. The results show that all of the novel derivatives were able to fold the single-stranded DNA sequences into antiparallel G-quadruplex structures, with derivative 15 exhibiting the highest stabilizing capability. Cell cycle analysis revealed that a primary trend of the "braco"-like derivatives was to arrest the cells in the S- and G 2M-phases of the cell cycle within the first 72 h, with derivative 13 and BRACO19 proving particularly effective in suppressing cell proliferation. All studies derivatives were less toxic to human fibroblast cell line in comparison with HT 29 cancer cell line.
- Ungvarsky, Jan,Plsikova, Jana,Janovec, Ladislav,Koval, Jan,Mikes, Jaromir,Mikesová, Lucia,Harvanova, Denisa,Fedorocko, Peter,Kristian, Pavol,Kasparkova, Jana,Brabec, Viktor,Vojtickova, Maria,Sabolova, Danica,Stramova, Zuzana,Rosocha, Jan,Imrich, Jan,Kozurkova, Maria
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- Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts
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A method for the Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle precatalysts (3a, 3b, and 3c). As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.
- Cheung, Chi Wai,Surry, David S.,Buchwald, Stephen L.
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supporting information
p. 3734 - 3737
(2013/08/23)
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- Synthesis, photophysical and NMR evaluations of thiourea-based anion receptors possessing an acetamide moiety
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The synthesis and photophysical evaluation of three diaryl thiourea-based anion receptors (4-6) for comparison with their urea counterparts (1-3) is outlined. These anion receptors posses an acetamide functionality on one of the aryl groups and an electron-withdrawing CF3 group on the other. By varying the position of the acetamide group, in the o-, m- and p-positions of 4-6, respectively, the anion binding ability was both tuneable and found to be, in some cases, significantly different from that seen for the urea analogues 1-3. The binding affinities of the receptors 4-6, as well as the binding stoichiometries, were evaluated using UV-vis absorption spectroscopy in MeCN. However, these receptors were not sufficiently emissive to quantify the anion recognition using fluorescence. The results confirmed strong binding of these receptors to anions such as fluoride, acetate, phosphate, pyrophosphate and chloride. Nevertheless, the overall results obtained did not conform to the anticipated trends seen for 1-3, which is most likely due to the enhanced binding affinity of the thiourea analogues 4-6. The binding interactions were also investigated by using 1H NMR which confirmed that these receptors interacted with the anions in a stepwise manner, where the primary anion binding interaction occurred at the thiourea side, which led to an activation of the acetamide moiety towards the second anion binding interaction, an example of an allosteric activation mode.
- Boyle, Elaine M.,McCabe, Thomas,Gunnlaugsson, Thorfinnur
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experimental part
p. 586 - 597
(2011/01/03)
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- Synthesis and fungicidal activity of novel aminophenazine-1-carboxylate derivatives
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A series of novel 6-aminophenazine-1-, 7-aminophenazine-1- and 8-aminophenazine-1-carboxylate derivatives were synthesized by a facile method, and their structures were characterized by 1H NMR, 13C NMR and high-resolution mass spectrometry. Some unexpected byproducts V-7b-V-8d were noticed and isolated, and their structures were identified by 2D NMR spectra including heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (Hmbc) and H-H correlation spectrometry (H-H COSY) approach. Their fungicidal activities against five fungi were evaluated, which indicated that most of the title compounds showed low fungicidal activities in vitro against Alternaria solanl, Cercospora arachidicola, Fusarium omysporum, Gibherella zeae, and Physalospora piricola at a dosage of 50 μg mL -1, while compounds IV-6a and IV-6b exhibited excellent activities against P. piricola at that dosage. Compound IV-6a could be considered as a leading structure for further design of fungicides. 2010 American Chemical Society.
- Wang, Ming-Zhong,Xu, Han,Yu, Shu-Jing,Feng, Qi,Wang, Su-Hua,Li, Zheng-Ming
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experimental part
p. 3651 - 3660
(2011/07/29)
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- The recognition and sensing of anions through "positive allosteric effects" using simple urea-amide receptors
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(Chemical Equation Presented) The design, synthesis, and X-ray crystallographic analysis of three simple diaryl-urea based anion receptors possessing an amide moiety on one of the aryl groups, and an electron withdrawing CF3 group on the other, is described. The three receptors differ only in the position of the amide functionality relative to the hydrogen bonding urea moiety (being para, meta, and ortho for 1, 2, and 3, respectively). This simple modification was shown to have a significant effect on the anion recognition ability, the strength of the recognition process, and the stoichiometry (host/guest) for these sensors. We demonstrate, by using both UV-vis absorption and 1H NMR spectroscopy, that these factors are caused by the ability of the amide moiety to both modulate the anion binding selectivity and the sensitivity of the urea moiety. We also demonstrate that, in the case of 1 and 2, this anion recognition at the urea moiety leads to concomitant activation (through enhanced inductive effect) in the amide functionality toward anions, which leads to the formation of an overall 1:2 (sensor/anion) binding stoichiometry for these receptors. This "activation" we describe as being an example of a "positive allosteric activation" by the urea site, caused directly by the first anion binding interaction, which to the best of our knowledge, has not been previously demonstrated for anion recognition and sensing.
- Dos Santos, Cidalia M. G.,McCabe, Thomas,Watson, Graeme W.,Kruger, Paul E.,Gunnlaugsson, Thorfinnur
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supporting information; experimental part
p. 9235 - 9244
(2009/04/06)
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- Selective reduction of aromatic nitro groups in the presence of amide functionality
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Pressure mediated selective reduction of aromatic nitro groups in the presence of amide functionality has been achieved by use of hydrazine hydrate.
- Deka, Dibakar Chandra,Kakati, Hari Sankar
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p. 223 - 224
(2007/10/03)
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- The inhibition of factor inhibiting hypoxia-inducible factor (FIH) by β-oxocarboxylic acids
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Cyclic β-oxocarboxylic acids inhibit factor inhibiting hypoxia-inducible factor via ligation to the active site iron. The Royal Society of Chemistry 2005.
- Banerji, Biswadip,Conejo-Garcia, Ana,McNeill, Luke A.,McDonough, Michael A.,Buck, Matthew R. G.,Hewitson, Kirsty S.,Oldham, Neil J.,Schofield, Christopher J.
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p. 5438 - 5440
(2008/01/27)
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- Bisphosphonate inhibition of the exopolyphosphatase activity of the Trypanosoma brucei soluble vacuolar pyrophosphatase
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Trypanosoma brucei, the causative agent of African trypanosomiasis, contains a soluble, vacuolar pyrophosphatase, TbVSP1, not present in humans, which is essential for the growth of bloodstream forms in their mammalian host. Here, we report the inhibition of a recombinant TbVSP1 expressed in Escherichia coli by a panel of 81 bisphosphonates. The IC50 values were found to vary from ～2 to 850 μM. We then used 3D QSAR (comparative molecular field and comparative molecular similarity index; CoMFA and CoMSIA) methods to analyze the enzyme inhibition results. The R2 values for the experimental versus the QSAR-predicted activities were 0.78 or 0.61 for CoMFA and 0.79 or 0.68 for CoMSIA, for two different alignments. The root-mean-square (rms) pIC50 error for the best CoMFA model was 0.41 for five test sets of five activity predictions, which translates to a factor of ～2.6 error in IC50 prediction. For CoMSIA, the rms pIC50 error and error factors were 0.35 and 2.2, respectively. In general, the most active compounds contained both a single aromatic ring and a hydrogen bond donor feature. Thirteen of the more potent compounds were then tested in vivo in a mouse model of T. brucei infection. The most active compound in vivo provided a 40% protection from death with no apparent side effects, suggesting that further development of such compounds may be of interest.
- Kotsikorou, Evangelia,Song, Yongcheng,Chan, Julian M. W.,Faelens, Stephanie,Tovian, Zev,Broderick, Erin,Bakalara, Norbert,Docampo, Roberta,Oldfield, Eric
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p. 6128 - 6139
(2007/10/03)
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- Highly efficient Beckmann rearrangement and dehydration of oximes
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Under mild conditions, Beckmann rearrangement of a variety of ketoximes could proceed in the presence of chlorosulfonic acid using toluene as a solvent with excellent conversion and selectivity. This procedure could also be applied in the dehydration of aldoximes for obtaining the corresponding nitriles.
- Li, Dongmei,Shi, Feng,Guo, Shu,Deng, Youquan
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p. 671 - 674
(2007/10/03)
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- N-Methylated diphenylguanidines: Conformations, propeller-type molecular chirality, and construction of water-soluble oligomers with multilayered aromatic structures
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The crystal structures of N,N'-diphenylguanidine (1) and its N-methylated derivatives were investigated, and the conformational properties of these molecules were utilized to construct water-soluble oligomers with multilayered aromatic structures. N,N'-Diphenylguanidine (1) afforded two types of crystals, chiral (P212121) and racemic (P2(1/c)), upon recrystallization from EtOH. In both crystals, 1 exists in the (E,Z) conformation, in which one C-N bond (length: 1.28-1.30 ?) attached to a phenyl ring shows double-bond character. In contrast, N,N'-dimethyl-N,N'-diphenylguanidine (4a) exists in the (Z,Z) conformation with the two aromatic rings facing each other. As judged from the crystal structures of several N-methylated compounds, the conformational preferences of diphenylguanidines appear to be related to those of aromatic anilides. N,N,N',N''-Tetramethyl-N',N''-diphenylguanidinium iodide (6) afforded chiral crystals, like 1 and N-methyl-N,N'-diphenylguanidine (2). The absolute structure of each enantiomeric propeller conformation of 6 was determined by X-ray analysis using the Bijvoet difference method. The Z-conformational preference of 4 allowed us to synthesize oligomeric di- or tetraguanidines (9-12) which have multilayered aromatic structures both as a crystal and in organic and aqueous solvents.
- Tanatani, Aya,Yamaguchi, Kentaro,Azumaya, Isao,Fukutomi, Ryuuta,Shudo, Koichi,Kagechika, Hiroyuki
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p. 6433 - 6442
(2007/10/03)
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- Phthalocyanine reactive dyestuffs
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Phthalocyanine reactive dyestuffs which, in the form of the free acid, have the formula (1) STR1 in which the variable radicals have the meaning given in the description, are prepared by condensation of the corresponding amines with cyanuric fluoride or cyanuric chloride in any desired order. The reactive dyestuffs according to the invention exhibit good wet and light fastness properties and are used for the dyeing and printing of cotton.
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- Reduction of Aromatic Nitro Compounds with Baker's Yeast
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The reduction of the nitro group of aromatic nitro compounds with baker's yeast was strongly influenced by the nature of the substituent on nitrobenzene, and in the reaction of acyl nitrobenzenes, selective reduction occurred to give optically active nitro alcohol and amino alcohol and amino ketone without giving any amino alcohol.Keywords baker's yeast; nitro compound; selective reduction; acyl nitrobenzene; chiral nitro alcohol
- Takeshita, Mitsuhiro,Yoshida, Sachiko,Kiya, Rieko,Higuchi, Naoko,Kobayashi, Yumi
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p. 615 - 617
(2007/10/02)
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- Reactive dyestuffs comprising a triazine moiety and a vinylsulfonyl moiety both being linked by a substituted alkylene bridge member
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A reactive dye of the formula STR1 in which: F is a radical selected from the group consisting of metal-free or metal-containing monoazo or disazo dyes containing at least one --SO3 H group, anthraquinone dyes, sulfophthalocyanine dyes, formazan dyes, phenazine dyes, oxazine dyes and nitroaryl dyes, R is hydrogen, C1 -C4 alkyl which is unsubstituted or substituted with --COOH or --SO3 H, cyanoethyl, or hydroxyethyl, X is fluorine, chlorine, bromine, --SO3 H, phenylsulfonyl or C1 -C4 -alkylsulfonyl, p is 1 or 2 and A is a radical of the formula STR2 in which: Y is chlorine, bromine, fluorine, --OH, --OSO3 H, --O-acyl, --CN, --COOH, --COO--C1 -C4 -alkyl, --CONH2 or --SO2 --Z, the group designated "alk" is a straight or branched polymethylene radical having 2 to 6 carbon atoms, V is STR3 hydrogen or C1 -C4 -alkyl which is unsubstituted or substituted by C1 -C2 -alkoxy, carboxyl, sulfo, halogen or hydroxy, Z is β-halogenoethyl, vinyl or β-acetoxyethyl, or A is a radical of the formulae STR4 in all of which R' is C1-6 -alkyl or hydrogen, Z is as defined above, o is 0 to 6, and m is 2 to 6.
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- Triazinyl reactive dyes containing additional fiber reactive groups bound through the sulfonylalkylaminoalkylamino bridge
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The invention relates to novel useful reactive dyes of the formula I STR1 in which: F is a radical selected from the group consisting of metal-free or metal-containing monoazo or disazo dyes containing at least one --SO3 H group, anthraquinone dyes, sulfophthalocyanine dyes, formazan dyes, phenazine dyes, oxanine dyes and nitroaryl dyes, R is hydrogen, C1 -C4 alkyl which is unsubstituted or substituted with --COOH or --SO3 H, cyanoethyl, or hydroxyethyl, X is fluorine, chlorine, bromine, --SO3 H, phenylsulfonyl or C1 -C4 -alkylsulfonyl, P is 1 or 2 and A is a radical of the formula STR2 in which: the groups designated "alk" are independently of each other straight or branched polymethylene radicals having 2 to 6 carbon atoms, and Z is β-halogenoethyl, vinyl, β-sulfatoethyl, β-thiosulfatoethyl or βacetoxyethyl.
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- Bisazo brown reactive dye
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A brown reactive dye represented by a free acid of the formula, STR1 wherein R is a hydrogen atom or a C1 to C4 alkyl group, X is --SO2 CH2 CH2 Cl, --SO2 CH=CH2, --SO2 CH2 CH2 OSO3 H or --SO2 CH2 CH2 OPO3 H2, rings A, B and C are each a benzene or naphthalene ring which may have other substituent, m is 0 to 3 and n is 0 to 1. This dye is suitable for dyeing cellulose fibers brown to afford dyeings superior in fastnesses, acid stability, build-up property and level dyeing property.
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- Fiber-reactive disazo brown dye having vinylsulfone-type reactive group
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A compound, or a salt thereof, represented by the following formula, STR1 wherein A is a substituted or unsubstituted phenylene or naphthylene group, B is STR2 in which R3 is a hydrogen atom or a lower alkyl, lower alkoxy, acylamino or ureido group, and R4 is a hydrogen atom or a lower alkyl or lower alkoxy group, R1 and R3 are independently a hydrogen atom or a substituted or unsubstituted lower alkyl group, X is a substituted or unsubstituted amino, lower alkoxy, substituted phenoxy or sulfo group, Y is --SO2 CH=CH2 or --SO2 CH2 CH2 Z, in which Z is a group capable of being split by the action of an alkali, and m is 2 or 3, which is useful for dyeing hydroxyl group- or amide group-containing fiber materials to give dyed products of a brown color having excellent fastness properties with good build-up property.
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- Synthesis and Spectral Characterization of Blue Dyes of the Benzene Series
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53 Donor-acceptor substituted azo dyes of the benzene series were prepared by diazonium-coupling reactions (1a-s) or halogen-cyanide exchange (->2a-x, 3a-j).Described are the preparation of the amines 4a-m and the coupling compounds 5a-t and the procedure of diazotizing and coupling.The colouristic and spectroscopic data show that compounds of the general formula 1 are excellent brilliant blue azo dyes usefull for dyeing polyester material.
- Thiel, W.,Mayer, R.,Jauer, E.-A.,Modrow, H.,Dost, H.
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p. 497 - 514
(2007/10/02)
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- Investigations of the Kinetics and Mechanism of Polarographic Reduction of o-, m- and p-Nitroacetanilides in Aqueous Ethanolic Medium
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Polarographic behaviour of o-, m- and p-nitroacetanilides in aqueous ethanolic solutions has been studied as a function of pH using NaNO3 (0.1 M) and Triton X-100 (0.001 percent) as the supporting electrolyte and maxima suppressor, respectively with a view to investigate the kinetics and mechanism of the reduction of o-, m- and p-nitroacetanilides at d.m.e.The reduction of the depolarizers has been found diffusion-controlled and irreversible.The potential-dependent rate constant, kf,h, has been calculated by Koutecky's method at different pH and the values of kinetic parameters (αna and k0f,h) have been calculated from log kf,h vs Ed,e plots which are linear thereby indicating that only a single rate-determining step is involved in the electrode process of each depolarizer.Based on the values of αna and the variation of E1/2 with pH, the stoichiometry of the rate-determining step involved in the reduction of each depolarizer at d.m.e. has been established.A tentative mechanism for the polarographic reduction of each depolarizer has been postulated.
- Singh, Mukhtar
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p. 737 - 740
(2007/10/02)
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- Process for the monoacylation of an aromatic primary diamine
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A process for the monoacylating of an aromatic primary diamine containing no anionic water-solubilizing group, preferably m-phenylene or p-phenylenediamine, which comprises reacting an acylating agent in aqueous medium with a mineral acid salt, preferably the hydrochloric acid salt, of the diamine wherein the reaction mixture is maintained at a pH of from 1.5 to 3.5 during the addition and reaction of the acylating agent.
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- 6-Anilino-1,4,5-trihydroxyanthraquinones
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Blue anthraquinone dyestuffs are prepared from the reaction of 6-chloro-1,4,5-trihydroxyanthraquinone with an appropriate aniline reactant. The resultant blue dyestuffs are 6-anilino-1,4,5-trihydroxyanthraquinones which produce excellent blue dyeings on polyester fabrics, particularly polyethylene terephthalate.
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