6306-70-3Relevant articles and documents
Crystal structures of some N-substituted 2,5-dimethylpyrrole derivatives
Jones, Peter G.,Ku?, Piotr,?annik, Mariusz,Kozik, Violetta
, p. 611 - 616 (2010)
The crystal and molecular structures of five di-(2,5-dimethylpyrrole) and one tri-(2,5-dimethylpyrrole) derivatives have been determined. These compounds were synthesized from the respective diamino derivatives and hexane-2,5-dione in direct and simple reactions. The molecular packings are largely based on C-H?π interactions.
Synthesis of Fe3O4@L-proline@SO3H as a novel and reusable acidic magnetic nanocatalyst and its application for the synthesis of N-substituted pyrroles at room temperature under ultrasonic irradiation and without solvent
Behbahani, Farahnaz K.,Shokri, Fatemeh
, (2021/08/18)
N-Substituted pyrroles have been prepared in high isolated yields (65–90%) by the reaction of hexane-2,5-dione with amines or diamines in the presence of Fe3O4@L-proline@SO3H at ambient temperature under ultrasonic irradiation and without solvent. The experimental procedure involves simple operations, and the products are readily separated by external magnet. The same reaction of hexane-2,5-dione with amines containing electron-acceptor substituents, such as 4-nitroaniline, resulted in fair yields of pyrrole derivatives.
Fe3O4@SiO2-PTMS-Guanidine-SA nanoparticles as an effective and reusable catalyst for the synthesis of N-substituted pyrroles
Rostami, Hedieh,Shiri, Lotfi
, p. 1329 - 1335 (2020/01/28)
Fe3O4@SiO2-PTMS-Guanidine-SA nanoparticles used as an effective catalyst for the synthesis of N-substituted pyrroles. Pyrroles were synthesized from the reaction between primary amine derivatives and 2,5-hexanedione with high to excellent yields under mild reaction conditions. After completion of the reaction, Fe3O4@SiO2-PTMS-Guanidine-SA magnetic nanoparticles could be recovered easily from the reaction mixture by an external magnet and reused. This catalyst was characterized by FT-IR spectroscopy, scanning electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, thermogravimetric analysis and vibrating-sample magnetometry techniques.
Sustainable Manganese-Catalyzed Solvent-Free Synthesis of Pyrroles from 1,4-Diols and Primary Amines
Borghs, Jannik C.,Lebedev, Yury,Rueping, Magnus,El-Sepelgy, Osama
supporting information, p. 70 - 74 (2019/01/11)
A general and selective metal-catalyzed conversion of biomass-derived primary diols and amines to the highly valuable 2,5-unsubstituted pyrroles has been developed. The reaction is catalyzed by a stable nonprecious manganese complex (1 mol %) in the absence of organic solvents whereby water and molecular hydrogen are the only side products. The manganese catalyst shows unprecedented selectivity, avoiding the formation of pyrrolidines, cyclic imides, and lactones.
A New Green and Efficient Br?nsted: Lewis Acidic DES for Pyrrole Synthesis
Shaibuna,Theresa, Letcy V.,Sreekumar
, p. 2359 - 2372 (2018/06/20)
Abstract: Deep eutectic solvents (DESs) are fluids composed of different Lewis or Br?nsted acids and bases, generally acknowledged as new analogues to ionic liquids (ILs), because of their similar characteristics, but with more advantages related to preparation cost, environmental impact etc. Their preparation involve the simple mixing of two components generally with moderate heating that are inexpensive, non-toxic, biodegradable and the resulting mixture is capable to overcome the drawbacks of conventional organic solvents and ILs. Chemical reactions with these materials are significantly less hazardous and they can act as catalysts as well as reaction media. Here, three new DESs based on ZrOCl2·8H2O in combination with urea, ethylene glycol and glycerol are introduced. Physicochemical properties like phase behaviour, Freezing point, density, viscosity, thermal stability and miscibility properties in common solvents are determined. In addition, a new method for the determination of acidity of DESs having both Br?nsted and Lewis sites is also introduced in this work. A convenient synthesis of pyrrole through Paal–Knorr reaction is reported using a variety of amines which are used to establish the importance of this catalyst in organic reactions. The products are analysed by GC–MS, 1H NMR and 13C NMR. By comparing the three DESs, DES 1 (formed from ZrOCl2·8H2O with urea) has the lowest density, viscosity, highest acidity and thermal stability. It was shown to be an excellent green catalyst for Paal–Knorr reaction. Reusability of the catalyst was also achieved up to 4 runs, without significant loss in its catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]
Efficient synthesis of substituted pyrroles through Pd(OCOCF3)2-catalyzed reaction of 5-hexen-2-one with primary amines
Chen, Xi,Yang, Meng,Zhou, Min
supporting information, p. 5215 - 5218 (2016/11/11)
An efficient and facile Pd(OCOCF3)2-catalyzed one-pot cascade protocol has been developed for the synthesis of multiple substituted pyrroles in good to excellent yields. Unlike the reported method starting from the 2-alkenal-1,3-carbonyl compounds, the process utilizes the less reactive 5-hexen-2-one and the method has great potential as a complement to the current developed methods.
The application of iron (III) phosphate in the synthesis of N-substituted pyrroles
Samadi, Marjan,Behbahani, Farahnaz K.
, p. 2881 - 2884 (2015/11/03)
A variety of N-substituted pyrroles have been prepared by reacting 2,5-hexadione with amines or diamines in the presence of iron (III) phosphate at room temperature under solvent-free conditions. The experiment protocol features simple operations, and the products are isolated in high yields (88-99%).
Sulfamic acid heterogenized on functionalized magnetic Fe3O4 nanoparticles with diaminoglyoxime as a green, efficient and reusable catalyst for one-pot synthesis of substituted pyrroles in aqueous phase
Veisi, Hojat,Mohammadi, Pourya,Gholami, Javad
, p. 868 - 873 (2015/02/19)
Surface functionalization of magnetic nanoparticles is an elegant way to bridge the gap between heterogeneous and homogeneous catalysis. We have conveniently loaded sulfonic acid groups on amino-functionalized Fe3O4 nanoparticles affording sulfamic acid-functionalized magnetic Fe3O4 nanoparticles (MNPs/DAG-SO3H) as an active and stable magnetically separable acidic nanocatalyst, which was characterized using X-ray diffraction, Fourier transform infrared and energy-dispersive X-ray spectroscopies, scanning and transmission electron microscopies, vibrating sample magnetometry and elemental analysis. The catalytic activity of MNPs/DAG-SO3H was probed through one-pot synthesis of N-substituted pyrroles from γ-diketones and primary amines in aqueous phase at room temperature. The heterogeneous catalyst could be recovered easily by applying an external magnet device and reused many times without significant loss of its catalytic activity.
Paal-knorr pyrrole synthesis in water
Akbaslar, Dilek,Demirkol, Onur,Giray, Sultan
supporting information, p. 1323 - 1332 (2014/04/17)
Water was a suitable medium for Paal-Knorr pyrrole cyclocondensation. Hexa-2,5-dione was reacted with several aliphatic and aromatic primary amines, affording N-substituted 2,5-dimethyl pyrrole derivatives in good to excellent yields. An efficient, green method using water either as environmentally friendly solvent or catalyst was presented.
Nanomagnetically modified sulfuric acid (γ-Fe2O 3@SiO2-OSO3H): An efficient, fast, and reusable catalyst for greener Paal-Knorr pyrrole synthesis
Cheraghi, Samaneh,Saberi, Dariush,Heydari, Akbar
, p. 1339 - 1343 (2014/07/21)
Paal-Knorr pyrrole synthesis was performed in the presence of superparamagnetic nanoparticles of modified sulfuric acid (γ-Fe 2O3@SiO2-OSO3H) as an efficient and magnetically separable catalyst. Recovery of the catalyst was simple using a magnet, allowing its reuse without significant loss of its catalytic activity (over five cycles).
