10149-93-6Relevant articles and documents
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 (2021)
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.
Two-Phase Electrochemical Generation of Aryldiazonium Salts: Application in Electrogenerated Copper-Catalyzed Sandmeyer Reactions
Goljani, Hamed,Tavakkoli, Zahra,Sadatnabi, Ali,Nematollahi, Davood
supporting information, p. 5920 - 5924 (2020/08/12)
The electrochemical generation of aryldiazonium salts from nitroarenes in a two-phase system (ethyl acetate/water) was reported for the first time. Some compounds including azo, azosulfone, and arylazides were prepared in good yields with good purity. Cathodically generated aryldiazoniums and anodically produced copper(Ι) ions were used to perform Sandmeyer reactions. To improve the method, an H-type self-driving cell equipped with a Zn rod as an anode was introduced and used for two-phase aryldiazonium production.
Continuous flow solvent free organic synthesis involving solids (reactants/products) using a screw reactor
Sharma, Brijesh M.,Atapalkar, Ranjit S.,Kulkarni, Amol A.
supporting information, p. 5639 - 5646 (2019/10/22)
Here we report for the first-time various organic transformations such as aldol condensation, oxidation, nucleophilic substitutions, protection, acylations and coupling reactions using a mechanochemical approach at a controlled temperature using a single synthesis platform. Almost minimal solvents or solvent-free conditions are used, making it a very efficient and clean synthesis of various products. A jacketed screw reactor when operated at different temperatures (0 °C to 160 °C) and over a range of rotation speeds for changing the residence time (15 s-300 s) helped to achieve maximum conversion. This approach is also extended to the synthesis using substrates having different substitutions, heterocycles and steric hindrance.
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
Mild preparation method for structural analogs of Sudan I
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Paragraph 0053-005, (2018/07/30)
The invention discloses a mild preparation method for structural analogs of Sudan I, and belongs to the technical field of organic chemistry. According to the method, dehydrogenation of N'-p-toluenesulfonyl aromatic hydrazine is promoted by utilizing alkali and oxygen in air to form an aryl diazo compound in situ; then a series of 1-aryl azo-2-naphthol Sudan I analogs are prepared by coupling with2-naphthol. By adopting the method disclosed by the invention, the strategy of producing an explosive intermediate in situ is used, so that 1-aryl azo-2-naphthol is conveniently and safely synthesized. The mild preparation method disclosed by the invention is mild in reaction conditions, wide in substrate applicability, simple and convenient to operate, lower in cost, less in by-products, high inproduct purity, and easy to separate and purify and can be suitable for relatively-large-scale preparation.
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.
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.]
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
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.
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.
