Disperse dyes based on 2-aminothiazole derivatives for cellulose triacetate fabric

A range of azo disperse dyes was prepared by coupling diazotized 2-amino-4-(p-nitrophenyl)-5-nitrothiazole with various substituted arylamines. Spectral properties in the infrared and visible range of the dyes obtained were investigated. All the dyes, when applied on cellulose triacetate fabric as 2% shade, showed fairly good to very good light fastness and very good to excellent fastness to washing, perspiration, rubbing and sublimation. All the dyes gave a wide range of reddish brown to indigo shades with very good depth and levelness on fabric. The purity of dyes was checked by thin layer chromatography. The percentage dyebath exhaustion and fixation on fabric was reasonably good and acceptable.     

Characterization,DFT calculations and dyeing performance on polyester fabrics of some azo disperse dyes containing pyrazole ring

A number of azo pyrazole derivatives and novel Schiff bases derived from azo diamino pyrazole were synthesized. These included 4-(2-arylhydrazono)-4H-pyrazole-3,5-diamines and N³,N⁵-dibenzylidene-4-(2-arylhydrazono)-4H-pyrazole-3,5-diamines. The chemical structures of the novel azo dyes were determined using UV–visible, IR, ¹H NMR, and ¹³C NMR spectroscopy. Dyeing process and tautomerism of the aforementioned azo compounds were predicted using DFT calculations. The electronic absorption spectra in methanol were observed and compared to those computed using B3LYP/6-31G(d,p). The dyeing performance of the produced disperse dyes was examined on polyester. The degree of exhaustion and the fastness properties of the dyed samples in terms of washing, perspiration, scorch, and light fastness were assessed. Moreover, the reflectance and color strength of the synthesized dyes were measured and discussed.     

Synthesis of some 4-arylazo-3-hydroxythiophene disperse dyes for dyeing polyester fabrics

A series of novel 4-arylazo-3-hydroxythiophene disperse dyes was synthesized by heterocyclization of ethyl 2-arylhydrazono-2-phenylthiocarbamoyl acetates with a variety of α-halogenated reagents. The structures of the synthesized dyes were confirmed by UV-Vis, IR, ¹H NMR, and MS spectroscopic techniques and elemental analysis. The dyes were applied to conventional polyester fabric by high temperature exhaust dyeing. These dyes were found to give orange to reddish-violet shades with very good depth, levelness, and brightness on polyester fabric. The dyed fabric showed moderate to good light fastness and very good fastness to washing and perspiration. Also the position of color in CIELAB coordinates (L^*, a^*, b^*, H^*, and C^*) was assessed. Correspondence: Ehab Abdel-Latif, Department of Chemistry, Faculty of Science, Mansoura University, 35516 Mansoura, Egypt     

Synthesis and dyeing performance of a novel polycarboxylic acid azo dye

A novel reactive polycarboxylic acid dye was synthesized by the reaction of polymaleic anhydride（PMA） with 3-methyl-1-（4- sulfonylphenyl）-4-（4-aminophenylazo）-2-pyrazoline-5-one.The structure of the novel dye was characterized by FTIR,UV-vis and ¹³C NMR spectra.The dyeing properties of dye on cotton were tested,and the novel dye possessed high fixation and good fastness.     

Synthesis and dyeing properties of new disazo disperse dyes for polyester and nylon fabrics

Diazotized aryl amines were coupled with two stenhouse salt namely, N-(5-phenylamino-penta-4-ol-2,4-diene-1-ylidene)anilines hydrochloride [S₁ (RH) or S₂ (ROH)] to furnish two series of disazo disperse dyes (S₁D_1–10 and S₂D_1–10). The structure of all the dyes was established by estimating number of azo groups, elemental analysis and spectral studies (IR, ¹H-NMR, UV/Visible). The structure–property relationship was discussed by using electronic absorption spectra of the dyes. These dyes were applied to polyester and nylon fabrics as disperse dyes by using temperature exhaust dyeing method. The relevant dyeing characteristics, such as dyeability on fabrics, wash-fastness and light-fastness were evaluated. Fabrics dyed with these dyes furnished generally deep and bright intense hues ranging from light yellow to orange to reddish brown. The color fastness of the dyed fabric was assessed by determining wash-fastness and light-fastness properties.     

Synthesis of some novel bis(hetaryl)azo disperse dyes and investigation of their absorption spectra

3‐Amino‐2‐cyano‐4,6‐disubstituted‐thieno{2,3‐b}pyridines and 3‐aminopyridine were diazotized and coupled with 2‐phenylindole, 2‐methylindole, and 1‐methyl‐2‐phenylindole, respectively. These dyes were characterized by UV‐Visible, FT‐IR, ¹H NMR, and mass spectroscopic techniques. Solvent effects on the visible absorption spectra of the dyes were evaluated. The color of the dyes is discussed with respect to the nature of the heterocyclic ring and substituent present therein. In addition, effects of temperature, concentration, as well as acid and base on the visible absorption maxima of the dyes are reported. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:622–630, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20361     

Synthesis and application of some novel fluorescent heterocyclic disperse dyestuffs based on phenothiazine on polyester

A series of novel heterocyclic disperse dyestuffs derived from phenothiazine were prepared by standard reactions from phenothiazine as the starting material. Phenothiazine was nitrated and oxidized then reduced to obtain synthesized disperse dyestuffs. The reaction conditions were varied in order to obtain optimal yields for each stage of the preparation to obtain the corresponding derivative and final disperse dyestuffs. All intermediates and disperse dyestuffs were purified and characterized by DSC, FTIR, ¹H NMR, ¹³C NMR, elemental analysis and UV–Visible spectroscopic techniques. The molar extinction coefficients (ε), wavelengths of maximum absorption (λ_max) and solvatochromism effects were studied in solvents as toluene, acetone and N,N-dimethylformamide (DMF). Results represented that the dyestuffs had extinction coefficients of 2011–28189 L mol⁻¹ cm⁻¹, wavelengths of maximum absorption of 448–475 nm in acetone and positive solvatochromism by changing solvent from toluene to DMF. The disperse dyestuffs were applied to locally manufactured polyester fibers and their dyeing properties were investigated. Results showed that the buildup of dyestuffs was acceptable and dyed fibers had very good heat and wash fastness and medium light fastness on polyester fibers.     

Synthesis of some novel heterocyclic dyes derived from pyrazole derivatives

Diazotized aryl amines were coupled with 3-substituted 5-amino pyrazoles to produce a series of novel 3-substituted 5-amino-4-arylazopyrazoles. Also, 3-substituted 5-amino-pyrazoles were diazotized and coupled with different phenols to give the corresponding novel 3-substituted 5-aryl azo pyrazoles. These dyes were characterized by elemental analysis and spectral data, applied to different types of fibres (wool, polyester and a blend of wool/polyester as disperse dyes) and their fastness properties were evaluated.     

Synthesis,characterization, and dyeing performance of some azo thienopyridine and thienopyrimidine dyes based on wool and nylon

A string of novel heterocyclic mono azo dyes were synthesized and their utilization in dyeing different fabrics as wool and nylon were discussed. Thienopyridine azo dyes 4 and 6 were prepared by reaction of chloro acetamidederivative 2 with diamino compounds to yield 3 and 5 , followed by reaction with NaNO₂/HCl and coupling with nucleophilic reagent. One-pot reaction of chloro acetamide 2 with ammonium thiocyanat in solvent ethanol gave the unexpected thienopyrimidine derivative 7 , which contain two active sites, the former is primary amine that was able to form diazonium salt that coupled with N,N-dimethylaniline, resorcinol, and/or self-coupling to afford the azo dyes 8-10 , and the latter is active methylene group that underwent coupling with different diazonium salts to give the azo thienopyrimidine derivative dye 11-15 . The dyeing performance of these azo dyes had been investigated in terms of their dyeing behavior and fastness properties on different fabrics. Results showed that the color strength (K/S) values, as well as, washing, rubbing, and resistance to acid, alkali and light showed high efficiency of these heterocyclic mono azo dyes to dye wool rather than nylon fibers.     

Synthesis of novel herbicidal sulfonylureas

Novel sulfonylurea derivatives containing flve-membered hete-rocycle 3a-1 and 4a-d were synthesized in good yields by the regioselective addition of aryl sulfonylisocyanates 1 to 5-amino-3-benzyl (aryl) thio-1, 2, 4-triazoles and its pyrazole analogues 2. The structures of all these compounds were evaluated by elemental analyses and 1H NMR spectroscopy. The preliminary biological tests showed that the products displayed herbiddal activity against rape to some extent.     

噻唑环衍生物的合成

噻唑环及其衍生物广泛存在于具有生物活性的分子中[1]可用于抗生素和消炎药的制备[2]。本文合成的几种噻唑基衍生物—类以HIV蛋白酶为靶点的新型抗艾滋病药物利托那韦的重要中间体[3-5],对其合成工艺的研究具有较实际的意义。噻唑环衍生物可通过α-卤代羰基化合物与硫代酰胺缩合而成[6],α-巯基酮与腈缩合反应得到,也可采用醛与半胱氨酸缩合,再与二氧化锰作用得噻唑类化合物[7]。本文采用α-氯代羰基类化合物与硫代酰胺缩合而得三种噻唑类化合物,产率较为理想。1合成路线设计合成路线设计可表示如下图1图1目标化合物的合成路线F ig.1 The …     

4-Hydroxy-2-quinolones. 90. Synthesis and antitubercular activity of 4-methyl-2-thiazolylamides of halo-substituted 4-hydroxy-2-oxo-1,2-dihydro-3-quinolinecarboxylic acids

Several variants were studied for the synthesis of esters of halogen derivatives of 4-hydroxy-2-oxo-1,2-dihydro-3-quinolinecarboxylic acids, whose reaction with 2-amino-4-methylthiazole gives the corresponding hetarylamides. Results are given for a study of the antitubercular activity of these products. Communication 89, see ref. [1]. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 71–76, January, 2006.     

反相离子对色谱法对两种新型苯磺酸类染料中间体的研究

用ZorbaxSBC18柱对2 氨基 4 氯 5 甲基苯磺酸和4 氨基 5 甲氧基 2 甲基苯磺酸两种新型染料中间体进行了反相离子对色谱法的研究。以甲醇和2mmol L四丁基溴化铵,5mmol L磷酸二氢钠溶液为流动相,紫外检测波长215nm。可在15min内对这两种染料中间体分别进行杂质检测和纯度分析。线性范围均为0.2～2.0μg,回归方程分别为Y=648.3 71.2ρ,r=0.9995;Y=177.3 65.0ρ,r=0.9994。该方法可用于对这两种染料中间体产品质量的监控及产品真伪的辨别。     

Synthesis of some novel pyrazolo[1,5-a]pyrimidine derivatives and their application as disperse dyes

A series of novel monoazo-disperse dyes containing pyrazolo[1,5-a]pyrimidine structures were synthesized starting with the coupling reaction between ethyl cyanoacetate and 4-hydroxybenzenediazonium chloride, followed by treatment of the resulting hydrazone product with hydrazine hydrate. The pyrazolohydrazone 6 is then treated with either 2,4-pentandione and enaminonitrile or aryl-substituted enaminoketones to give the target pyrazolo[1,5-a]pyrimidine dyes 7 and 15a-d. Structural assignments to the dyes were made using NMR spectroscopic methods. A new high temperature method, using microwave heating, was employed to apply these dyes to polyester fibers. Most of the dyed fabrics tested displayed moderate light fastness and excellent washing fastness properties.     

Synthesis and characterization of some novel ruthenium(II) complexes containing thiolate ligands

Reactions of the ruthenium complexes [RuH(CO)Cl(PPh₃)₃] and [RuCl₂(PPh₃)₃] with hetero-difunctional S,N-donor ligands 2-mercapto-5-methyl-1,3,5-thiadiazole (HL¹), 2-mercapto-4-methyl-5-thiazoleacetic acid (HL²), and 2-mercaptobenzothiazole (HL³) have been investigated. Neutral complexes [RuCl(CO)(PPh₃)₂(HL¹)] (1), [RuCl(CO)(PPh₃)₂(HL²)] (2), [RuCl(CO)(PPh₃)₂(HL³)] (3), [Ru(PPh₃)₂(HL¹)₂] (4), [RuCl(PPh₃)₃(HL²)] (5), and [RuCl(PPh₃)₃(HL³)] (6) imparting κ²-S,N-bonded ligands have been isolated from these reactions. Complexes 1 and 4 reacted with diphenyl-2-pyridylphosphine (PPh₂Py) to give neutral κ¹-P bonded complexes [RuCl(CO)(κ¹-P-PPh₂Py)₂(HL¹)] (7), and [Ru(κ¹-P-PPh₂Py)₂(HL¹)₂] (8). Complexes 1-8 have been characterized by analytical, spectral (IR, NMR, and electronic absorption) and electrochemical studies. Molecular structures of 1, 2, 4, and 7 have been determined crystallographically. Crystal structure determination revealed coordination of the mercapto-thiadiazole ligands (HL¹-HL³) to ruthenium as κ²-N,S-thiolates and presence of rare intermolecular S-S weak bonding interaction in complex 1.     

Synthesis,characterization and dyeing assessment of novel acid azo dyes and mordent acid azo dyes based on 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid on wool and silk fabrics

Novel acid mono azo and mordent acid mono azo dyes were synthesized by the coupling of diazonium salt solution of different aromatic amines with 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid. The resulting dyes were characterized by spectral techniques like elemental analysis, IR, ¹H-NMR and UV visible spectroscopy. The dyeing performance of all the dyes was evaluated on wool and silk fabrics. The dyeing of chrome pre-treated wool and silk fabrics showed better hues on mordented fabrics. Dyeing of wool and silk fabrics resulted in pinkish blue to red shades with very good depth and levelness. The dyed fabrics showed excellent to very good light, washing, perspiration, sublimation and rubbing fastness.     

Synthesis of 6-chloro and 6-fluoro-4-hydroxyl-2-quinolone and their azo disperse dyes

<正>In this study,6-chloro-4-hydroxy-2-quinolone and 6-flouro-4-hydroxy-2-quinolone were synthesized from corresponding dianilides.These compounds were coupled with some diazotized aromatic amines to give the corresponding azo disperse dyes.The structures of the quinolone derivatives and new azo dyes were confirmed by UV-vis,FT-IR,~1H NMR and elemental analysis.     

Synthesis and antioxidant properties of some new thiazolyl coumarin derivatives

ABSTRACT

A three-component one-pot synthesis of new thiazolyl coumarin derivatives was carried out by condensing 3-acetyl-4-hydroxycoumarin, arylaldehydes, thiourea and ammonium acetate at reflux in DMC. The optimization details of the developed novel protocol are recorded. In addition, we have also synthesized these compounds via another second route in two steps. High atom-economy, excellent yields, simple procedure, and mild reaction conditions are the important features of this one-pot protocol. The chemical structures of the newly synthesized compounds were elucidated by using analytical (IR, ¹H NMR, ¹³C NMR). Further, all the compounds were screened for their antioxidant activities.     

Synthesis of 3-acetyl-2-amino-4-pyridone

A method hxsynthesizing 3-acetyl-2-amino-4-pyyridone has been suggested. The synthesis involves the condensation of dimethylformamide dimethylacetal at the NH₂ group of diphenylboron chelate diacetylketene aminal followed by its intramolecular cyclization under the action of NaOMe in MeOH.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 177–179. January, 1996.     

Synthesis of some novel divalent transition metal complexes as antimicrobials

A novel series of transition metal complexes have been synthesized from the reaction of 5-((3-(methylthio)-5-(pyridin-4-yl)-4H- 1,2,4-triazol-4-ylamino)melhyl)quinolm-8-ol with transition metal salts.The structures of these compounds have been elucidated by elemental and spectral analysis.Furthermore,compounds were screened for in vitro antimicrobial activity against the representative panel of two Gram-positive and two Gram-negative bacteria and two strains of fungus.The various compounds show potent inhibitory action against test organisms.