2703-27-7Relevant academic research and scientific papers
The selective synthesis ofN-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents
Chen, Po-Yi,Hsu, Chi-Wei,Ho, Tong-Ing,Ho, Jinn-Hsuan
, p. 6662 - 6666 (2021/02/21)
The solvent-controllable photoreaction of 4-methoxyazobenzenes to afford 1-aryl-1H-benzimidazoles orN-arylbenzene-1,2-diamines has been studied. The irradiation of 4-methoxyazobenzenes in DMF containing 0.5 M hydrochloric acid providedN2-aryl-4-methoxybenzene-1,2-diamines as the major product, while irradiation in acetal containing 0.16 M hydrochloric acid led to 1-aryl-6-methoxy-2-methyl-1H-benzimidazoles as the major product. A possible reaction mechanism explaining the selectivity was also discussed.
Effect of flexible chain on mesomorphic properties of alkyloxy substituted 4-chloroazobenzene liquid crystals
Kamruzzaman,Roushown,Karim, Rabiul,Chowdhury, Samiul Islam,Hasan, Tariqul
, p. 1159 - 1164 (2021/05/10)
Three rod-shaped alkyloxy substituted 4-chloroazobenzene liquid crystals, 1-(4-chlorophenyl)-2-[4-(alkyloxy)phenyl]diazene (hexayl, octyl and nonyl as flexible oxyalkyl chain) have been synthesized by diazotization of p-chloroaniline with phenol and subse
Novel Phenyldiazenyl Fibrate Analogues as PPAR α/γ/δ Pan-Agonists for the Amelioration of Metabolic Syndrome
Giampietro, Letizia,Laghezza, Antonio,Cerchia, Carmen,Florio, Rosalba,Recinella, Lucia,Capone, Fabio,Ammazzalorso, Alessandra,Bruno, Isabella,De Filippis, Barbara,Fantacuzzi, Marialuigia,Ferrante, Claudio,MacCallini, Cristina,Tortorella, Paolo,Verginelli, Fabio,Brunetti, Luigi,Cama, Alessandro,Amoroso, Rosa,Loiodice, Fulvio,Lavecchia, Antonio
supporting information, p. 545 - 551 (2019/03/19)
The development of PPARα/γ dual or PPARα/γ/δ pan-agonists could represent an efficacious approach for a simultaneous pharmacological intervention on carbohydrate and lipid metabolism. Two series of new phenyldiazenyl fibrate derivatives of GL479, a previously reported PPARα/γ dual agonist, were synthesized and tested. Compound 12a was identified as a PPAR pan-agonist with moderate and balanced activity on the three PPAR isoforms (α, γ, δ). Moreover, docking experiments showed that 12a adopts a different binding mode in PPARγ compared to PPARα or PPARδ, providing a structural basis for further structure-guided design of PPAR pan-agonists. The beneficial effects of 12a were evaluated both in vitro, on the expression of PPAR target key metabolic genes, and ex vivo in two rat tissue inflammatory models. The obtained results allow considering this compound as an interesting lead for the development of a new class of PPAR pan-agonists endowed with an activation profile exploitable for therapy of metabolic syndrome.
Azo Dyes: New Palladium- and Copper-Catalysed Coupling Reactions on an Old Template
Rasheed, Omer K.,Quayle, Peter
, p. 2608 - 2616 (2018/05/25)
The elaboration of azo dyes using a variety of transition-metal-catalysed reactions (Stille, Heck, Ullmann, and Suzuki couplings) is reported. This methodology has been applied to the synthesis of functionalised coumarin azo dye conjugates, substrates which may find potential application in the development of new sensors.
Synthesis and anticancer activities of 4-[(Halophenyl)diazenyl]phenol and 4-[(Halophenyl)diazenyl]phenyl aspirinate derivatives against nasopharyngeal cancer cell lines
Ho, Boon Kui,Ngaini, Zainab,Neilsen, Paul Matthew,Hwang, Siaw San,Linton, Reagan Entigu,Kong, Ee Ling,Lee, Boon Kiat
, (2017/08/18)
Aspirin and azo derivatives have been widely studied and have drawn considerable attention due to diverse biological activities. In this study, a series of 4-[(halophenyl)diazenyl]phenyl aspirinate derivatives were synthesized from the reaction of aspirin
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.
Nano-CuFe2O4-supported sulfonic acid as a novel and recyclable nanomagnetic acid for diazotization of aromatic amines: efficient synthesis of various azo dyes
Nemati, Firouzeh,Elhampour, Ali,Natanzi, Mahshid B.,Sabaqian, Samaneh
, p. 1045 - 1054 (2016/05/02)
Abstract: A novel heterogeneous sulfonic acid functionalized nanomagnetic CuFe2O4 was successfully prepared and characterized by analyzing different obtained data including Fourier transform infrared spectroscopy, X-ray powder diffraction, field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, dynamic light scattering and vibrating sample magnetometer. Then the novel acidic reagent was examined in synthesis of various azo-containing compounds from coupling of aryl diazonium ferrite sulfate salts with aromatic and non-aromatic compounds. The procedure starts by diazotization of aromatic amines with NaNO2 and wet CuFe2O4–SO3H and then coupling reaction of aryl diazonium ferrite sulfate salts with appropriate reagent. The prepared nano-solid acid showed high activity in synthesis of variety of aryl diazonium salts. In addition the as-prepared aryl diazonium ferrite sulfate salts are stable at room temperature for many hours and reacted efficiently in coupling reactions of aryl diazonium salts. All the azo dyes are synthesized in high yields and simple reaction conditions at room temperature. Moreover, the nanomagnetic solid acid was easily recovered from the reaction mixture and reused five runs without significant loss of activity. Graphical Abstract: [Figure not available: see fulltext.]
A New Benzannulation Reaction of Azoaromatics
Rasheed, Omer K.,Raftery, James,Quayle, Peter
supporting information, p. 2806 - 2810 (2015/12/18)
The BHQ benzannulation reaction of azo-substituted (2-allylaryl)trichloracetates, leading to azo-naphthalenes, is described. The scope and limitations of this new synthesis of azoaromatics is discussed.
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.
New fluorescent symmetrically substituted perylene-3,4,9,10-dianhydride- azohybrid dyes: Synthesis and spectroscopic studies
Saeed, Aamer,Shabir, Ghulam
, p. 7 - 12 (2014/06/24)
Five phenolic azo-dyes (3a-e) were synthesized by diazo coupling of the suitably substituted anilines (1a-e) with phenol at low temperature in alkaline medium. The resulting dyes have low solubility in aqueous medium due to lack of carboxylic or sulfonic
