7014-14-4Relevant academic research and scientific papers
Access to azolopyrimidine-6,7-diamines as a valuable “building-blocks” to develop new fused heteroaromatic systems
Gazizov, Denis A.,Fedotov, Victor V.,Chistyakov, Konstantin A.,Gorbunov, Evgeny B.,Rusinov, Gennady L.,Charushin, Valery N.
, (2021/06/07)
A simple and convenient approach for the synthesis of new azolopyrimidine-6,7-diamines has been developed by the method of reductive cleavage of azo-group in series 6-[2-(4-methylphenyl)diazenyl]azolo[1,5-a]pyrimidine-7-amines, which was obtained by the interaction of aminoazoles with [2-(4-methylphenyl)hydrazinylidene]-3-oxo-propionitrile. The proposed approach allows to use a wide range of aminoazoles as a starting reagent and it also distinguishes itself by the simplicity of isolation and purification of products. The synthetic potential of presented diamines was demonstrated by the reaction of obtaining azolo[a]annulated pteridines.
A facile synthesis of formazan dyes conjugated with plasmonic nanoparticles as photosensitizers in photodynamic therapy against leukemia cell line
Khalifa, Mohamed E.,Elkhawass, Elham A.,Pardede, Antoni,Ninomiya, Masayuki,Tanaka, Kaori,Koketsu, Mamoru
, p. 2195 - 2206 (2018/11/10)
Abstract: A series of 1,5-bis(4-aryl/heteryl)-3-cyanoformazan derivatives was synthesized and characterized by spectral analysis. The synthesis strategy involved an easy and practical diazo coupling of different aryl (heteryl) diazonium salts with cyanoacetic acid. The synthesized compounds were electrostatically conjugated to gold and/or silver nanoparticles in dimethylsulfoxide and were examined as photosensitizers for photodynamic therapy (PDT). The PDT activity of the formazan derivatives alone and conjugated with metal nanoparticles was investigated against HL-60 cells under dark and light conditions. Formazan derivatives and their conjugates showed variable promising anticancer activity in dark and light conditions related to their structures. The interaction of synthesized formazan derivatives with metal nanoparticles enhanced the light absorption of the dyes and thus showed remarkable increase in PDT against cancer cells. Graphical abstract: [Figure not available: see fulltext.].
Synthesis and spectral properties of symmetrical and asymmetrical 3-Cyano-1,5-diarylformazan dyestuffs for dyeing polyester fabrics
Khattab, Tawfik A.,Haggag, Karima M.
, p. 33 - 40 (2018/05/28)
IN THIS study, we report on a general synthetic approach to both symmetrical and asymmetrical 3-cyano-1,5-diarylformazan dyes. The reaction of enaminonitrile with aromatic diazonium salts in slightly acidic medium affords arylhydrazonals as stable intermediate that are readily converted into asymmetrical formazans via second azo-coupling in a weak alkaline medium. Symmetrical formazan dyestuffs are synthesized directly via double azo-coupling of the key intermediate 3-piperidinylacrylonitrile with the corresponding diazonium salts in weak alkaline medium using sodium acetate as a weak base. The structures of the prepared dyestuffs and intermediates are demonstrated by elemental analysis (C, H, N),1H and13C NMR, FTIR and GC-MS spectroscopic techniques. The prepared formazan disperse colorants are applied to dye polyester fabric to give satisfactory fastness properties to wash, perspiration, rubbing and light.
Microwave-Assisted Synthesis of Arylazoaminopyrazoles as Disperse Dyes for Textile Printing
Khattab, Tawfik A.,Haggag, Karima M.,Elnagdi, Mohamed H.,Abdelrahman, Amal A.,Abdelmoez Aly, Sherif
, p. 766 - 772 (2016/07/11)
The synthesis of heterocyclic azo-dyes via conventional heating and microwave (MW) heating was investigated. From a sequence of reactions starting from cyanoacetic acid, 4-arylazo-2H-pyrazol-3-ylamines and 4-arylazo-2-phenyl-2H-pyrazol-3-ylamines were obtained. The structures these compounds were obtained by inspection of spectroscopic and analytical techniques including1H and13C NMR spectroscopy, IR spectroscopy, mass spectrometry, and elemental analysis. The fastness properties and UV/Vis absorption spectroscopic data of these disperse dyes in printing polyester fabrics were investigated.
Reactions of Methylenedisulfonyldi(acetic acid) Derivatives with Arenediazonium Salts and Aromatic Aldehydes
Bazavova, I. M.,Esipenko, A. N.,Neplyuev, V. M.,Lozinskii, M. O.
, p. 520 - 524 (2007/10/03)
Reactions of methylenedisulfonyldiacetonitrile with arenediazonium salts in weakly alkaline medium yield mixtures of 1,5-bis(arylhydrazono)-1,5-dicyano-2,4-dithiapentane 2,2,4,4-tetraoxides and 1,5-diaryl-3-cyanoformazans.Under the same conditions, dimethyl methylenedisulfonyldiacetate yields mainly 1,5-bis(arylhydrazono)-1,5-bis(methoxycarbonyl)-2,4-dithiapentane 2,2,4,4-tetraoxides, whereas methylenedisulfonyldiacetamide reacts with elimination of the carbamoyl groups to give 1,1',5,5'-tetraaryl-3,3'-methylenedisulfonyldiformazans.Methylenedisulfonyldiacetonitrile reacts with aromatic aldehydes with formation of 1,7-diaryl-2,6-dicyano-3,5-dithia-1,6-heptadiene 3,3,5,5-tetraoxides.
Convenient Synthesis of 3-Arylazopyrazoles and 2-Arylazo-1,3,4-Δ2-Thiadiazoline Derivatives from 3-Nitroformazans
Abdelhamid, Abdou O.,Abbas, Ikhlass M.,Abdallah, Magda A.,Fahmi, Abdelgawad A.,Shawali, Ahmad S.
, p. 813 - 816 (2007/10/02)
Reactions of 3-nitro-1,5-diarylformazans 1a-c with carbanions of acetylacetone, dibenzoylmethane, acetoacetanilide, benzoylacetonitrile, ω-benzenesulfonylacetophenone and malononitrile yielded the corresponding 3-arylazopyrazole derivatives 4-9 respective
