6756-41-8Relevant academic research and scientific papers
One-pot synthesis of azo compounds in the absence of acidic or alkaline additives
Cheng, Xin-Wang,Duan, Pan,Liu, Ting-Ting,Yan, Jiao-Zhao,Zeng, Yao-Fu
, p. 486 - 490 (2020/10/22)
A one-pot method for the synthesis of azo compounds by the reaction of β-naphthol with aryl amines using t-BuONO as the nitrosonium source in DCM at room temperature was developed. This method features mild reaction conditions, a simple experimental procedure, and is free of acidic or alkaline additives.
Novel chromenes and benzochromenes bearing arylazo moiety: molecular docking, in-silico admet, in-vitro antimicrobial and anticancer screening
Afifi, Tarek H.,Riyadh, Sayed M.,Deawaly, Anwar A.,Naqvi, Arshi
, p. 1471 - 1487 (2019/07/08)
Novel derivatives of benzochromene 9a–e and chromene 10a–e were synthesized via multi components reaction that utilizes azo dyes, malononitrile, and arylaldehydes as starting materials. The structures of the newly synthesized compounds were elucidated by the IR, 1H-NMR, 13C-NMR and mass spectral data. The new synthesized compounds were explored for their in-silico ADMET properties. The docking investigations verified good docking outcomes in terms of score and binding affinities of the examined compounds on the desired proteins, namely the GlcN-6-P synthase and PI3Ks. The in-vitro studies, which encompassed the antibacterial activity against two types of Gm +ve and two of Gm –ve, and the antifungal activity against four fungi micro-organisms were evaluated by the well diffusion method for the synthesized compounds. Moreover, the anticancer activity was tested against three human carcinoma cell lines [human colon carcinoma (HCT-116), human breast adenocarcinoma (MCF-7), and liver carcinoma (HEPG-2)], exhibiting promising anticancer activity in comparison to Vinblastine, Colchicine and Doxorubicin as standard drugs. The data suggests that some of the new derivatives of chromene scaffold which emerged promising in the in-silico molecular docking studies displayed good in-vitro antimicrobial and anticancer activities and could be exploited as leads for further optimization.
An environmentally friendly approach to the green synthesis of azo dyes with aryltriazenes via ionic liquid promoted C-N bonds formation
Zhang, Yonghong,Liu, Yonghong,Ma, Xiaoqian,Ma, Xia,Wang, Bin,Li, Hongguang,Huang, Yan,Liu, Chenjiang
, p. 438 - 444 (2018/06/14)
An efficient and green approach for the synthesis of azo dyes has been developed via the Br?nsted acidic ionic liquid (IL) promoted diazo coupling reaction of naphthols with aryltriazenes. The reaction was carried out with the aryltriazenes as diazotizing
New generation of nitrite functionalized star-like polyvinyl imidazolium compound: Application as a nitrosonium source and three dimensional nanocatalyst for the synthesis of azo dyes
Shomali, Ashkan,Valizadeh, Hassan,Noorshargh, Saeideh
, p. 409 - 418 (2017/07/24)
The compounds with three-dimensional and ionic structures have attracted considerable attentions because of their unique characteristics as a drug carrier and catalyst. Star-like poly ionic compounds are a new generation of three-dimensional structures which have both; the exclusive ionic features and three-dimensional structures. Recently, we reported the synthesis of diazonium salts from aniline derivatives using carboxyl and nitrite functionalized graphene quantum dots. Methods: Nitrite-functionalized star-like polyionic (NFSP) compound was synthesized as a new generation of three-dimensional nanocatalyst. Herein, the use of NFSP as an efficient reagent and nanocatalyst for the diazotization of aniline derivatives and subsequent synthesis of azo dyes via the reaction with active phenolates under solvent-free conditions was reported. Results: In order to demonstrate the positive impact of NFSP efficiency, the reaction times and yields of the products were compared with other methods and catalysts which have been reported previously. The brilliant performance of NFSP can be ascribed to multifunctional reagent and also trapping the ingredient within catalyst cavities. Conclusion: A highly effective and cost-effective method has been developed for the preparation of azo dyes. In reported method, new three-dimensional catalyst with highly ionic characteristic and multifunctional nitrosonium source is available. These special features reduced the required amount of catalyst, reaction time and also increased the efficiency of catalyst.
Convenient and rapid diazotization and diazo coupling reaction via aryl diazonium nanomagnetic sulfate under solvent-free conditions at room temperature
Koukabi, Nadiya,Otokesh, Somayeh,Kolvari, Eskandar,Amoozadeh, Ali
, p. 12 - 17 (2015/10/05)
For the first time, nanomagnetic-supported sulfonic acid is used for conversion of several types of aromatic amine, containing electron-withdrawing groups as well as electron-donating groups to the corresponding azo dyes in excellent yield. The synthesis of these compounds is described by the sequential diazotization-diazo coupling of various aromatic amines with sodium nitrite, nanomagnetic supported sulfonic acid and coupling agents under solvent-free conditions at room temperature. This new method offers several advantages including short reaction time, mild reaction conditions, avoidance of harmful acids, and simple work-up procedure. More importantly, aryldiazonium salts supported on magnetic nanoparticles (aryl diazonium nanomagnetic sulfate) were sufficiently stable to be kept at room temperature in the dry state.
Synthesis of a nitrite functionalized star-like poly ionic compound as a highly efficient nitrosonium source and catalyst for the diazotization of anilines and subsequent facile synthesis of azo dyes under solvent-free conditions
Valizadeh, Hassan,Shomali, Ashkan,Ghorbani, Jalal,Noorshargh, Saeideh
, p. 64 - 71 (2015/03/04)
Nitrite functionalized star-like poly ionic (NFSPI) compound was synthesized and used as a highly efficient nitrosonium source and catalyst for the conversion of aniline derivatives to diazonium salts. Azo dyes were prepared via in situ azo-coupling reaction of these diazoniums with active aromatic compounds under solvent-free conditions in very short reaction time in excellent yields. NFSPI plays dual role as a three-dimensional nitrosonium source and catalyst because of its poly ionic characteristic. The isolated products were confirmed with FT-IR spectrum, 1H-NMR, 13C-NMR spectroscopy and CHNSO analysis. The structure of heterogeneous reagent and catalyst was confirmed by FT-IR spectrum, SEM images, EDX and CHNSO analysis. Yields and reaction times for the synthesis of a variety of products via this procedure were compared with reported values in literature.
An environmentally friendly approach to the green synthesis of azo dyes in the presence of magnetic solid acid catalysts
Safari, Javad,Zarnegar, Zohre
, p. 17738 - 17745 (2015/06/15)
A solvent-free, efficient and green approach for the synthesis of azo dyes has been developed by the diazo coupling reactions of aromatic amines with β-naphthol in the presence of sulfonic acid functionalized magnetic Fe3O4 nanoparticles (Fe3O4@SiO2-SO3H) by a grinding method at room temperature. This green methodology aims to overcome the limitations and drawbacks of the previously reported methods such as low temperature, use of acids, alkalis and toxic solvents, instability of diazonium salts at room temperature, modest yields, and long reaction times. Moreover, the attractive advantages of the process include mild conditions with excellent conversions, simple product isolation process, inexpensive procedure and recyclability of the magnetic catalyst. This journal is
Substituent effect on the tautomerization of 1-arylazonaphthalen-2-ols by mass spectrometric analysis
Lin, Shaw-Tao,Lin, Lee-Hui,Lin, Yi-Cang,Ding, Mei-Fan
, p. 257 - 262 (2015/03/31)
An electron-ionization (EI) mass spectra of a series of 1-arylazonaphthalen-2-ols was obtained for studying the substituent effect on the fragmentation. The correlation between the ratio, molecular ion and fragment ion, and Hammett's constants is applied to examine the effect of the substituent on the fragmentation. The negative correction between the ratio, Imolecular ion/(I171amu + I143amu + I115amu), and Hammett's constants indicates an electron-withdrawing group destabilized the molecular ion. An unusual long-range hydrogen transfer demonstrates an important role in the fragmentation process Mass spectra of a series of 1-arylazonaphthalen-2-ols were obtained for studying the substituent effect on the fragmentation. The correlation between the ratio of molecular ion and fragment ion, and Hammett's constants is applied to examine the effect of substituent on the fragmentation. The negative correction indicates an electron-with-drawing group destabilized the molecular ion. An unusual long-range hydrogen transfer demonstrates an important role in the fragmentation process.
Genetic incorporation of a 2-naphthol group into proteins for site-specific azo coupling
Chen, Shuo,Tsao, Meng-Lin
, p. 1645 - 1649 (2013/11/06)
The 2-naphthol analogue of tyrosine, 2-amino-3-(6-hydroxy-2-naphthyl) propanoic acid (NpOH), has been genetically introduced into proteins in Escherichia coli. This is achieved through the directed evolution of orthogonal aminoacyl-tRNA synthetase/tRNA pairs that selectively charge the target amino acid in response to the amber stop codon, UAG. Moreover, chemoselective azo coupling reactions have been revealed between the 2-naphthol group and diazotized aniline derivatives that are substituted with an electron donating moiety. The coupling reactions required a very mild condition (pH 7) with great reaction rate (less than 2 h at 0 C), high efficiency, and excellent selectivity.
Fe(HSO4)3 as an Efficient Catalyst for Diazotization and Diazo Coupling Reactions
Rahimizadeh, Mohammad,Eshghi, Hossein,Shiri, Ali,Ghadamyari, Zohreh,Matin, Maryam M.,Oroojalian, Fatemeh,Pordeli, Parvaneh
, p. 716 - 719 (2013/05/08)
Diazo coupling reactions of aromatic amines with 2-naphthol in a green, efficient and easy procedure is described. Ferric hydrogensulfate catalyses this reaction in water at room temperature and short reaction time with high yields. The antibacterial activities of the synthesized compounds against four pathogenic bacteria are also investigated.
