- Crystal structures of some N-substituted 2,5-dimethylpyrrole derivatives
-
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.
- Jones, Peter G.,Ku?, Piotr,?annik, Mariusz,Kozik, Violetta
-
-
Read Online
- 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
-
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.
- Behbahani, Farahnaz K.,Shokri, Fatemeh
-
-
- Fe3O4@SiO2-PTMS-Guanidine-SA nanoparticles as an effective and reusable catalyst for the synthesis of N-substituted pyrroles
-
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.
- Rostami, Hedieh,Shiri, Lotfi
-
p. 1329 - 1335
(2020/01/28)
-
- Sustainable Manganese-Catalyzed Solvent-Free Synthesis of Pyrroles from 1,4-Diols and Primary Amines
-
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.
- Borghs, Jannik C.,Lebedev, Yury,Rueping, Magnus,El-Sepelgy, Osama
-
supporting information
p. 70 - 74
(2019/01/11)
-
- A New Green and Efficient Br?nsted: Lewis Acidic DES for Pyrrole Synthesis
-
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.]
- Shaibuna,Theresa, Letcy V.,Sreekumar
-
p. 2359 - 2372
(2018/06/20)
-
- Efficient synthesis of substituted pyrroles through Pd(OCOCF3)2-catalyzed reaction of 5-hexen-2-one with primary amines
-
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.
- Chen, Xi,Yang, Meng,Zhou, Min
-
supporting information
p. 5215 - 5218
(2016/11/11)
-
- The application of iron (III) phosphate in the synthesis of N-substituted pyrroles
-
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%).
- Samadi, Marjan,Behbahani, Farahnaz K.
-
p. 2881 - 2884
(2015/11/03)
-
- 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
-
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.
- Veisi, Hojat,Mohammadi, Pourya,Gholami, Javad
-
p. 868 - 873
(2015/02/19)
-
- Paal-knorr pyrrole synthesis in water
-
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.
- Akbaslar, Dilek,Demirkol, Onur,Giray, Sultan
-
supporting information
p. 1323 - 1332
(2014/04/17)
-
- Nanomagnetically modified sulfuric acid (γ-Fe2O 3@SiO2-OSO3H): An efficient, fast, and reusable catalyst for greener Paal-Knorr pyrrole synthesis
-
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).
- Cheraghi, Samaneh,Saberi, Dariush,Heydari, Akbar
-
p. 1339 - 1343
(2014/07/21)
-
- An efficient and green procedure for synthesis of pyrrole derivatives by Paal-Knorr condensation using sodium dodecyl sulfate in aqueous micellar
-
A simple, economical, and green approach to the synthesis of N-substituted pyrroles using sodium dodecyl sulfate as surfactant in water is described. The experiment protocol features simple operations, and the products are isolated in high to excellent yields (60-98%).
- Veisi, Hojat,Azadbakht, Reza,Ezadifar, Mehdi,Hemmati, Saba
-
p. E241-E246
(2013/06/04)
-
- One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, and Paal-Knorr synthesis of pyrrole derivatives catalyzed by TCCA
-
A convenient synthesis of sulfonic esters from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with trichloroisocyanuric acid (TCCA), tetra-butylammonium chloride (t-Bu4NCl), and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of N-substituted pyrroles by the reaction of hexane-2,5-dione with primary amines has been accomplished using TCCA as a catalyst under mild condition with excellent yields.
- Hemmati, Saba,Mojtahedi, Mohammad Majid,Abaee, Mohammad Saeed,Vafajoo, Zahra,Saremi, Shokufe Ghahri,Noroozi, Mohammad,Sedrpoushan, Alireza,Ataee, Meral
-
p. 347 - 357
(2013/09/23)
-
- 1-Methylimidazolium hydrogen sulfate catalyzed convenient synthesis of 2,5-dimethyl-N-substituted pyrroles under ultrasonic irradiation
-
Ionic liquid [HMIM]HSO4 was found to be an efficient catalyst for the synthesis of N-substituted pyrroles through the reaction of 2,5-hexanedione with amines under ultrasonic irradiation at room temperature. These reactions proceed with good yields under short reaction time. Furthermore, the green catalytic system can be recycled specific times with no decreases in yields and reaction rates.
- Li, Daqing,Zang, Hongjun,Wu, Changchun,Yu, Nianqin
-
p. 1144 - 1148
(2013/06/27)
-
- Xanthan sulfuric acid as an efficient, green, biodegradable, and recyclable solid acid catalyst for one-pot synthesis of N-substituted pyrroles under solvent-free conditions at room temperature
-
A new, green, and efficient method for synthesis of a variety of N-substituted pyrroles from condensation reactions of 2,5-hexanedione with amines or diamines using xanthan sulfuric acid as a biosupported and reusable ecofriendly catalyst under solvent-free conditions at room temperature is described. The use of a nontoxic, inexpensive, easily available, and reusable biosupported proton source catalyst under solvent-free conditions makes this protocol practical, environmentally friendly, and economically attractive.
- Rahmatpour, Ali
-
experimental part
p. 491 - 495
(2012/06/16)
-
- Polystyrene-supported GaCl3 as a highly efficient and recyclable heterogeneous Lewis acid catalyst for one-pot synthesis of N-substituted pyrroles
-
A new and environmentally benign method for the preparation of N-substituted pyrroles from one-pot condensation reaction of 2,5-hexanedione with amines and diamines in the presence of polystyrene-supported gallium trichloride (PS/GaCl3) as a highly active and reusable heterogeneous Lewis acid catalyst is presented. This new protocol has the advantages of easy availability, stability, reusability and eco-friendly of the catalyst, high to excellent yields, simple experimental and work-up procedure.
- Rahmatpour, Ali
-
experimental part
p. 15 - 19
(2012/07/03)
-
- Cellulose sulfuric acid as a biodegradable and recoverable solid acid catalyst for one pot synthesis of substituted pyrroles under solvent-free conditions at room temperature
-
A new and efficient method for the preparation of N-substituted pyrroles from one-pot condensation reaction of 2,5-hexandione with amines and diamines in the presence of cellulose sulfuric acid (CSA) as a bio-supported catalyst at room temperature under solvent-free conditions is presented. This new protocol has the advantages of easy availability, stability, reusability and eco-friendly of the catalyst, high to excellent yields, simple experimental and work-up procedure.
- Rahmatpour, Ali
-
experimental part
p. 80 - 83
(2012/01/12)
-
- ZrOCl2·8H2O as a highly efficient, eco-friendly and recyclable Lewis acid catalyst for one-pot synthesis of N-substituted pyrroles under solvent-free conditions at room temperature
-
A new and efficient method for the synthesis of a variety of N-substituted pyrroles from condensation reactions of 2,5-hexanedione with amines or diamines using ZrOCl2·8H2O as a water-tolerant Lewis acid catalyst at room temperature is described.The use of nontoxic, inexpensive, easily available and reusable catalyst under solvent-free conditions make this protocol practical, environmentally friendly and economically attractive.
- Rahmatpour, Ali
-
experimental part
p. 585 - 590
(2011/10/18)
-
- One-pot synthesis of N-substituted pyrroles catalyzed by polystyrene-supported aluminum chloride as a reusable heterogeneous Lewis acid catalyst
-
A convenient and efficient procedure is presented for the one-pot synthesis of N-substituted pyrroles by condensation of 2,5-hexandione and amines or diamines in the presence of cross-linked polystyrene-supported aluminum chloride (PS/AlCl3) as a highly active and reusable heterogeneous Lewis acid catalyst. This polymeric solid acid catalyst is stable and can be easily recovered and reused without appreciable change in its efficiency.
- Rahmatpour, Ali,Aalaie, Jamal
-
experimental part
p. 85 - 90
(2011/10/09)
-
- Ultrasound-assisted synthesis of 2,5-dimethyl-N-substituted pyrroles catalyzed by uranyl nitrate hexahydrate
-
An efficient synthesis of different novel 2,5-dimethyl-N-substituted pyrrole derivatives by the Paal-Knorr condensation has been accomplished using uranyl nitrate hexahydrate as catalyst under soft conditions and ultrasonic irradiation. The synthesized compounds were confirmed through spectral characterization using IR, 1H NMR, 13C NMR and mass spectra.
- Satyanarayana,Sivakumar
-
experimental part
p. 917 - 922
(2012/03/08)
-
- Silica sulfuric acid (SSA) as a solid acid heterogeneous catalyst for one-pot synthesis of substituted pyrroles under solvent-free conditions at room temperature
-
A variety of N-substituted pyrroles have been synthesized by reacting γ-diketones with amines, diamines or triamine in the presence of silica sulfuric acid (SSA) at room temperature under solvent-free conditions. The experiment protocol features simple operations, and the products are isolated in high to excellent yields (70-98%).
- Veisi, Hojat
-
scheme or table
p. 2109 - 2114
(2010/06/14)
-
- A convenient synthesis of pyrroles catalyzed by acidic resin under solvent-free condition
-
A convenient and effective Paal-Knorr condensations of 2,5-hexanedione with most amines have been carried out at room temperature under solvent-free condition. Macroporous strongly acidic styrol resin (D001) as a novel, efficient, cost-effective, and reusable solid acid catalyst for the synthesis of pyrroles under the same conditions. The pyrroles were obtained in high yields in short reaction times.
- Yuan, Shi Zhen,Liu, Jin,Xu, Ling
-
experimental part
p. 664 - 668
(2011/10/12)
-
- One-pot synthesis of substituted pyrroles with N, N, N', N' -tetrachlorobenzene-1, 3-disulphonamide and N, N'-diiodo-N, N' -1, 2-ethanediylbis(p-toluenesulphonamide) as novel catalytic reagents
-
In this research, N, N, N'N'-tetrachlorobenzene-1, 3-disulphonamide as novel catalytic reagent and 2V,2V'-diiodo-2V,2V'-1, 2-ethane- diylfeis(p-toluenesulphonamide) as new catalyst were used for the synthesis of V-substituted pyrroles in good to excellent yields under mild conditions. These reusable reagents were compared with existing reagents and it is clear that this study is a welcome addition in the field of pyrrole synthesis.
- Ghorbani-Vaghei, Ramin,Veisi, Hojat
-
experimental part
p. 33 - 38
(2010/08/07)
-
- Approach to synthesis of Β-enamino ketones and pyrroles catalyzed by gallium(III) triflate under solvent-free conditions
-
Metal triflates have been used to catalyze synthesis of-enamino ketones or pyrroles from amines and 1,3-dicarbonyl or 1,4-dicarbonyl compounds under solvent-free conditions, respectively. Among different metal triflates screened, 0.5mol% Ga(OTf)3 efficiently promoted the reactions to give excellent yields. In addition, the catalyst could be recovered easily after the reactions and reused without evident loss in activity.
- Chen, Jiuxi,Yang, Xiaoliang,Liu, Miaochang,Wu, Huayue,Ding, Jinchang,Su, Weike
-
experimental part
p. 4180 - 4198
(2010/01/15)
-
- An approach to the Paal-Knorr pyrroles synthesis catalyzed by Sc(OTf)3 under solvent-free conditions
-
A facile synthesis of N-substituted pyrroles by the Paal-Knorr condensation has been accomplished using a simple procedure. Among different metal triflates screened, 1 mol % Sc(OTf)3 efficiently promoted the reaction to give excellent yield (89-98%) under mild reaction conditions. Additionally, Sc(OTf)3 could be recovered easily after the reactions and reused without evident loss in activity.
- Chen, Jiuxi,Wu, Huayue,Zheng, Zhiguo,Jin, Can,Zhang, Xingxian,Su, Weike
-
p. 5383 - 5387
(2007/10/03)
-
- A straightforward highly efficient Paal-Knorr synthesis of pyrroles
-
A straightforward simple synthesis of substituted pyrroles using bismuth nitrate-catalyzed modified Paal-Knorr method has been accomplished with an excellent yield. This method produces pyrroles with multicyclic aromatic amines.
- Banik, Bimal K.,Banik, Indrani,Renteria, Mercy,Dasgupta, Swapan K.
-
p. 2643 - 2645
(2007/10/03)
-
- Simple Synthesis of Substituted Pyrroles
-
Simple synthesis of substituted pyrroles using iodine-catalyzed and montmorillonite KSF-clay-induced modified Paal-Knorr methods has been accomplished with excellent yields. N-Substituted carbazole has also been prepared by following this method. If one of the reactants is a liquid, the reaction proceeds exceedingly well without a solvent. This method gives pyrroles with less nucleophilic multicyclic aromatic amines at room temperature.
- Banik, Bimal K.,Samajdar, Susanta,Banik, Indrani
-
p. 213 - 216
(2007/10/03)
-
- Montmorillonite KSF-mediated facile synthesis of pyrroles
-
A facile synthesis of substituted pyrroles over montmorrilonite KSF clay has been accomplished in excellent yield.
- Samajdar, Susanta,Becker, Frederick B.,Banik, Bimal K.
-
p. 1019 - 1022
(2007/10/03)
-
- An Electron Spin Resonance Study of the Radical Cations of Pyrroles, Furans, and Thiophenes in Liquid Solution
-
Photolysis of alkylpyrroles in trifluoroacetic acid containing mercury(II) trifluoroacetate, alkylfurans in trifluoroacetic acid, or alkylthiophenes in sulphuric acid, induces oxidation to the corresponding radical cations.The e.s.r. spectra show that the electronic configuration is similar in all three species, the unpaired electron occupying the φA MO in which the heteroatom lies in a nodal plane.Photolysis of 2,6-dimethyl- and 2,6-diethyl-thiophene in trifluoroacetic acid containing mercury(II) trifluoroacetate, on the other hand, gave rise to spectra with a high g value (2.0062), showing hyperfine coupling to two non-equivalent pairs of alkyl groups in an unsymmetrical dimer.
- Davies, Alwyn G.,Julia, Luis,Yazdi, Safieh N.
-
p. 239 - 244
(2007/10/02)
-
- Pyrrole and Pyrazole Ring Closure in Heterogeneous Media
-
Pyrroles and pyrazoles may be conveniently prepared by dispersing primary amines or hydrazines and 1,4- or 1,3-diketones, respectively, on alumina or clay (montmorillonite K 10) without solvent, keeping the mixture at 20 deg C or higher temperatures for 1-26 h, and then eluting the product with dichloromethane.
- Texier-Boullet, F.,Klein, B.,Hamelin, J.
-
p. 409 - 411
(2007/10/02)
-