14909-79-6Relevant academic research and scientific papers
Microwave-assisted aminolysis of epoxides under solvent-free conditions catalyzed by montmorillonite clay
Mojtahedi, Mohammad M.,Saidi, Mohammad R.,Bolourtchian, Mohammad
, p. 128 - 129 (1999)
The reaction of primary and secondary amines with epoxides in the presence of montmorillonite K10 clay, under solvent-free conditions and microwave irradiation affords high yields of β-amino alcohols.
Synthesis and application of Cu(II) immobilized MCM-41 based solid Lewis acid catalyst for aminolysis reaction under solvent-free condition
Chaudhary, Garima,Gupta, Neha,Singh, Amit Pratap
, (2021/07/22)
In this paper, a Cu(II) immobilized periodic mesoporous organosilica (PMOs) was synthesized and used as a reusable solid Lewis acid catalyst for the aminolysis of epoxides under solvent-free conditions. An amide-based ligand, L-propylsilyl (1) having a specific binding pocket was prepared and fabricated on mesoporous MCM-41 to produce mesoporous organosilica L-propylsilyl@MCM-41 (2). Further, it has been utilized for anchoring Cu(II) ions under controlled reaction conditions to yield solid Lewis acid catalyst Cu(II)-L-propylsilyl@MCM-41 (3). The synthesized catalyst 3 exhibits significantly higher catalytic activity for aminolysis compared to hitherto known solid Lewis acid catalysts. An extensive range of β-amino alcohols with high regio and stereoselectivity were prepared by using catalyst 3. The catalyst was recovered easily and reused eight times without any loss in its catalytic activity. Furthermore, the synthesis of clinically significant propranolol (β-blocker) from α- naphthyl glycidyl ether was attained successfully using catalyst 3 in a very decent yield.
M-Type SrFe12O19Ferrite: An Efficient Catalyst for the Synthesis of Amino Alcohols under Solvent-Free Conditions
Laayati, Mouhsine,Hasnaoui, Ali,Abdallah, Nayad,Oubaassine, Saadia,Fkhar, Lahcen,Mounkachi, Omar,El Houssame, Soufiane,Ait Ali, Mustapha,El Firdoussi, Larbi
, (2020/08/05)
Magnetically separable strontium hexaferrite SrFe12O19 was prepared using the chemical coprecipitation method, and the nanostructured material was characterized by X-ray diffraction, scanning electron microscopy (SEM), energy-dispersive spectrometry (EDS), and BET analysis. The SEM images showed the homogeneity of the chemical composition of SrFe12O19 and uniform distribution of size and morphology. The pore size of the nanomaterial and its specific area were determined by BET measurements. Strontium hexaferrite SrFe12O19 exhibited a strong magnetic field, which is highly suitable in the heterogeneous catalysis as it can be efficiently separated from the reaction. The magnetic nanocatalyst showed high activity and environmentally benign heterogeneous catalysts for the epoxide ring-opening with amines affording β-amino alcohols under solvent-free conditions. When unsymmetrical epoxides were treated in the presence of aromatics amines, the regioselectivity was influenced by the electronic and steric factors. Total regioselectivity was observed for the reactions performed with aliphatic amines. The magnetically SrFe12O19 nanocatalyst showed excellent recyclability with continuously good catalytic activities after four cycles.
Synthesis and structure of an air-stable bis(pentamethylcyclopentadienyl) zirconium pentafluorbezenesulfonate and its application in catalytic epoxide ring-opening reactions
Li, Ningbo,Wang, Lingxiao,Wang, Haojiang,Qiao, Jie,Zhao, Wenjie,Xu, Xinhua,Liang, Zhiwu
, p. 1033 - 1039 (2018/02/06)
An air-stable mononuclear complex of bis(pentamethylcyclopentadienyl) zirconium pentafluorbezenesulfonate was successfully synthesized by treating C6F5SO3Ag with [(CH3)5Cp]2ZrCl2, which showed the cationic uninuclear structure of [{(CH3)5Cp}2Zr(CH3CN)2(H2O)][OSO2C6F5]2·CH3CN (1) confirmed by the X-ray analysis. Complex 1 was also characterized by other techniques and found to have the good nature of air-stability, water tolerance, thermally-stability and strong Lewis-acidity. Moreover, the complex showed high catalytic activity and recyclability in catalytic epoxide ring-opening reactions by amines or alcohols. This catalytic system affords a simple and efficient approach for synthesis of β-amino alcohols or β-alkoxy alcohols.
Tetragonal versus hexagonal: Structure-dependent catalytic activity of Co/Zn bimetallic metal-organic frameworks
Pariyar, Anand,Asl, Hooman Yaghoobnejad,Choudhury, Amitava
, p. 9250 - 9257 (2016/09/28)
Tetragonal and hexagonal phases of monometallic Zn and bimetallic Co/Zn metal-organic frameworks (MOFs), with secondary building units (SBUs) containing a M3O (M = metal) cluster, were synthesized from identical constituents using a benzenetricarboxylate (BTC3-) linker that forms decorated 3,6- and 3,5-connected networks, respectively. There exist subtle differences between the SBUs; one of the metal atoms in the M3O cluster in the tetragonal phase has one dissociable DMF solvent molecule while that in the hexagonal phase has three. Connectivities between the SBUs form one-dimensional channels in both MOFs. These MOFs catalyze the chemoselective addition of amines to epoxides, giving exclusively β-hydroxyamine under heterogeneous conditions. A ring-opening reaction of a symmetrical epoxide showed that the hexagonal phase diastereoselectively yields trans-alcohol, exhibiting an exquisite model for structure-dependent activity.
Mild regiospecific alcoholysis and aminolysis of epoxides catalyzed by zirconium(IV) oxynitrate
Shinde, Sandip S.,Said, Madhukar S.,Surwase, Trupti B.,Kumar, Pradeep
supporting information, p. 5916 - 5919 (2015/11/02)
A regiospecific method for the ring-opening reaction of epoxides by the primary, secondary, tertiary alcohols, and aryl, aliphatic amines has been developed using non-toxic metal nitrate salt as a catalyst. The best results were obtained using zirconium(IV) oxynitrate among the various screened metal nitrate salts. The reported protocol works efficiently for styrene epoxide and aliphatic as well.
Mesoporous Titania-Iron(III) Oxide with Nanoscale Porosity and High Catalytic Activity for the Synthesis of β-Amino Alcohols and Benzimidazole Derivatives
Roy, Susmita,Banerjee, Biplab,Salam, Noor,Bhaumik, Asim,Islam, Sk. Manirul
, p. 2689 - 2697 (2015/09/15)
A mesoporous TiO2-Fe2O3 mixed oxide material (MTF-1E) with nanoscale porosity and a high BET surface area was synthesized using sodium dodecyl sulfate (SDS) as a structure-directing agent. The material was characterized by
N-Fluorobenzenaminium tetrafluoroborate generated in situ by aniline and Selectfluor as a reusable catalyst for the ring opening of epoxides with amines under microwave irradiation
Chauhan, Manmohan Singh,Yadav, Geeta Devi,Hussain, Firasat,Singh, Surendra
, p. 3945 - 3952 (2015/02/19)
The ring opening of epoxides with aromatic and aliphatic amines was carried out under solvent free conditions using N-fluorobenzenaminium tetrafluoroborate (2 mol%) generated in situ by the reaction of aniline and Selectfluor as a catalyst with microwave irradiation. Excellent yields of β-amino alcohols were obtained. The catalyst also results in the retention of the stereochemistry for the ring opening of enantiopure epoxide with amine. The catalyst was recovered and reused up to 4 cycles for the ring opening of cyclohexene oxide with aniline. This journal is
An efficient protocol for regioselective ring opening of epoxides using sulfated tungstate: Application in synthesis of active pharmaceutical ingredients atenolol, propranolol and ranolazine
Pathare, Sagar P.,Akamanchi, Krishnacharya G.
supporting information, p. 6455 - 6459 (2013/11/19)
Sulfated tungstate was found to be a new and highly efficient catalyst for opening of epoxide rings by amines to give β-amino alcohols with high regioselectivity. Various advantages associated with this novel and environmental friendly protocol include solvent-free conditions, short reaction times, high product yields, simple workup procedure and easy recovery and reusability of the catalyst. This protocol has been applied for the synthesis of active pharmaceutical ingredients atenolol, propranolol and ranolazine.
In vivo antifilarial activity of some cyclic and acylic alcohols
Agarwal, Alka,Awasthi, Satish K.,Murthy
experimental part, p. 430 - 434 (2012/04/18)
The filarial nematodes, Wuchereria bancrofti, Brugia malayi, and Brugia timori are the causative agents of lymphatic filariasis. 2-Substituted propanol, cyclohexanol, and cyclooctanol compounds were evaluated for microfilaricidal and macrofilaricidal activity in vivo against Acanthocheilonema viteae and Litomosoides carinii in rodents. In the cyclohexanol series, 2-(piperidin-1-yl) cyclohexanol (2b) showed 88.9% macrofilaricidal activity against A. viteae in vivo, while cyclooctanol series, 2-(4- benzyl piperdin-1-yl) cyclooctanol (2f) showed 100% macrofilaricidal activity against A. viteae. Further, compounds 1-(furan-2-ylamino) ethanol (4a) and 1-(4-benzylpiperidin- 1-yl)-ethyl acetate (5b) showed 81.3% and 83.4% macrofilaricidal activity, respectively, against the same parasite. Interestingly, compounds 2f and 4a showed significant sterilization of female worms in A. viteae. However, these compounds were found inactive against L. carinii. Therefore, the new class of compounds appeared to have promising antifilarial activity.
