6273-87-6Relevant academic research and scientific papers
Cross-linked poly(N-vinylpyrrolidone)-titanium tetrachloride complex: A novel stable solid TiCl4 equivalent as a recyclable polymeric Lewis acid catalyst for regioselective ring-opening alcoholysis of epoxides
Rahmatpour, Ali,Sajjadinezhad, Seyed Mehrzad
, (2021/08/09)
Cross-linked poly(N-vinylpyrrolidone) resin beads were prepared as macromolecular ligand precursors by suspension copolymerization of N-vinyl-2-pyrrolidone and N,N′-methylenebisacrylamide (MBA) as a crosslinking agent in water. Subsequently, the resulting polymer carrier precursor was readily combined with titanium tetrachloride to form a stable polymeric coordination complex (PNVP/TiCl4), and this novel stable TiCl4 equivalent evaluated as a heterogeneous and reusable solid Lewis acid catalyst for the regio-and stereoselective nucleophilic ring opening of various epoxides with various alcohols to prepare β-alkoxy alcohols in excellent yields without generating any waste. The MBA-cross-linked PNVP and resultant catalyst were characterized by Fourier transform infrared spectroscopy (FT–IR), field-emission scanning electron microscope (FE–SEM), energy dispersive X-ray (EDX), inductively coupled plasma (ICP), and thermogravimetric analysis (TGA) techniques. Moreover, the catalyst is very stable, easily separated, and reused at least five times without significant loss of activity. In terms of scope, yields, the amount of catalyst used, and reaction time, the PNVP-TiCl4 complex catalyst is an improvement over previously reported heterogeneous catalysts for ring opening of epoxides methods. Further, the experimental outcome revealed that using the copolymer beads as carriers with a high percentage of crosslinking and the high mesh size leads had an adverse effect on the reaction rate.
A Thiophene-2-carboxamide-Functionalized Zr(IV) Organic Framework as a Prolific and Recyclable Heterogeneous Catalyst for Regioselective Ring Opening of Epoxides
Das, Aniruddha,Anbu, Nagaraj,Reinsch, Helge,Dhakshinamoorthy, Amarajothi,Biswas, Shyam
, p. 16581 - 16591 (2019/12/04)
A new thiophene-2-carboxamide-functionalized Zr-UiO-66 MOF (1) was synthesized by employing a traditional solvothermal procedure. Compound 1 displayed high thermal (up to 340 °C under an Ar atmosphere) and chemical stability (in water, 1 M HCl, and acetic acid). A nitrogen physisorption measurement with the activated form of 1 (denoted 1) exhibited a BET surface area (781 m2/g) despite attachment of a bulky side chain with the linker molecule. Compound 1 was able to heterogeneously catalyze the ring-opening reaction of epoxides with amines. Catalyst 1 exhibited significant yields as well as wide substrate scope in the ring opening of epoxides by means of amines. It also displayed better catalytic performance in comparison to known MOF catalysts such as Cu3(BTC)2, Fe(BTC) (BTC: 1, 3, 5-benzenetricarboxylate), and Zr-UiO-66. Control experiments were performed with free linker, Zr(IV) salt and without catalyst 1, confirming the exclusive role of 1 in the catalytic reaction. The reusability characteristics of catalyst 1 was established for up to five consecutive catalytic cycles. The synthesis and characterization of the linker molecule, material 1, and 1 and mechanism of the catalysis reaction were studied elaborately.
Robust and Environmentally Benign Solid Acid Intercalation Catalysts for the Aminolysis of Epoxides
Li, Tengfei,Jin, Lin,Zhang, Wei,Miras, Haralampos N.,Song, Yu-Fei
, p. 4699 - 4706 (2018/09/25)
The catalytic aminolysis of epoxides can lead to a large number of β-amino alcohols which are of particular interest in industrial applications. In this paper, we demonstrate for the first time the use of a polyoxometalate [CoW12O40]
β-amino alcohols and their respective 2-phenyl-N-alkyl aziridines as potential DNA minor groove binders
Vaidergorn, Miguel M.,Carneiro, Zumira A.,Lopes, Carla D.,de Albuquerque, Sérgio,Reis, Felipe C.C.,Nikolaou, Sofia,Mello, Juliana F.R. e,Genesi, Giovani L.,Trossini, Gustavo H.G.,Ganesan,Emery, Flavio S.
, p. 657 - 664 (2018/08/23)
It is known that aziridines and nitrogen mustards exert their biological activities, especially in chemotherapy, via DNA alkylation. The studied scaffold, 2-phenyl-1-aziridine, provides a distinct conformation compared to commonly used aziridines, and the
Post-synthesis of Zr-MOR as a robust solid acid catalyst for the ring-opening aminolysis of epoxides
Tang, Bo,Song, Wei-Chao,Li, Sheng-Yang,Yang, En-Cui,Zhao, Xiao-Jun
, p. 13503 - 13511 (2018/08/21)
Zirconosilicate with the MOR topology (Zr-MOR) was successfully prepared using a two-step post-synthesis strategy from pre-dealumination of a H-MOR zeolite and subsequent dry impregnation of Cp2ZrCl2. The incorporated Zr species main
Highly efficient and green chemical synthesis of imidazolyl alcohols and N-imidazolyl functionalized β-amino compounds using nanocrystalline ZSM-5 catalysts
Kore, Rajkumar,Satpati, Biswarup,Srivastava, Rajendra
, p. 8 - 17 (2014/04/03)
A solvent free protocol is developed for the synthesis of imidazolyl alcohols and N-imidazolyl functionalized β-amino compounds. Imidazolyl alcohols were synthesized by the ring opening of epoxides with imidazoles and N-imidazolyl functionalized β-amino compounds were synthesized by the hydroamination reaction of imidazoles and activated olefins. These reactions were catalyzed by a variety of crystalline heterogeneous catalysts such as Al/Zr substituted nanocrystalline ZSM-5 (M-Nano-ZSM-5), conventional M-ZSM-5 (where M = Zr, Al), and Zr substituted amorphous mesoporous catalysts (Zr-SBA-15 and Zr-KIT-6). Among these catalysts, nanocrystalline Zr-Nano-ZSM-5 exhibited the highest activity and regioselectivity. Structure activity relationship is explained based on the catalytic activity, acidity measurements, reactivity of reactants (imidazoles/epoxides/methyl acrylate), competitive adsorption, nature, and type of catalysts. Zr-Nano-ZSM-5 exhibited exceptionally high catalytic activity compared to the catalysts reported in the literature for the synthesis of imidazolyl alcohols and other imidazole derivatives.
Highly efficient nanocrystalline zirconosilicate catalysts for the aminolysis, alcoholysis, and hydroamination reactions
Kore, Rajkumar,Srivastava, Rajendra,Satpati, Biswarup
, p. 2891 - 2904 (2014/01/06)
Nanocrystalline zirconosilicates and titanosilicates with MFI framework structure were hydrothermally synthesized by the addition of organosilanes in the synthesis composition of conventional zirconosilicate and titanosilicate materials. Materials were characterized by a complementary combination of X-ray diffraction, nitrogen sorption, scanning/transmission electron microscopy (S/TEM), ammonia temperature-programmed desorption (TPD), Fourier transform infrared (FT-IR) spectroscopy, and ultraviolet-visible (UV-vis) spectroscopic investigations. Nanocrystalline zeolite catalysts of the present study are reusable. They exhibit significantly higher catalytic activities in aminolysis and alcoholysis compared with the hitherto known catalysts. A range of β-amino alcohols/β-alkoxy alcohols with high regioselectivity were synthesized using zirconosilicates. Application of these materials was also extended in the synthesis of aminoesters by the hydroamination reaction of methyl acrylates and amines. Structure activity relationship was explained based on acidity measurements, reactivity of amines/alcohols, and adsorption of reactants on catalysts.
Synthesis, characterisation and cardiac activity of some novel 2,3-substituted-4-phenyl-1,3-oxazolidine derivatives
Gudaprthi, Vijayalakshmi,Bharathi,Omprakash
, p. 765 - 769 (2011/12/16)
A series of 2,3-substituted-4-phenyl-1,3-oxazolidine derivatives were synthesized from DL-(±)-phenyl glycine. DL-(±)-Phenyl glycine was reduced to the corresponding alcohol, which was then condensed with different aldehydes to form Schiff bases, which are then educed and further condensed with different substituted aldehydes to give the oxazolidine derivatives. The synthesized compounds are characterized by 1H NMR, IR and mass spectral analysis. All the compounds were investigated for cardiac activity while all the compounds show significant activity.
Thiourea catalyzed aminolysis of epoxides under solvent free conditions. Electronic control of regioselective ring opening
Chimni, Swapandeep Singh,Bala, Neeraj,Dixit, Vaibhav A.,Bharatam, Prasad V.
experimental part, p. 3042 - 3049 (2010/06/14)
A reactant economizing process for the regioselective aminolysis of epoxides using equimolar quantities of reactants catalyzed by the double hydrogen bond donor N,N′-bis[3,5-bis(trifluoromethyl)phenyl]thiourea is reported. Regioselectivity of the reaction
Highly efficient and versatile chemoselective addition of amines to epoxides in water catalyzed by erbium(III) triflate
Procopio, Antonio,Gaspari, Marco,Nardi, Monica,Oliverio, Manuela,Rosati, Ornelio
, p. 2289 - 2293 (2008/09/18)
Er(OTf)3 is proposed as a highly efficient and reusable catalyst for the opening of epoxides in water with aliphatic as well as aromatic amines leading to the synthesis of β-amino alcohols. The aqueous conditions employed in the present method will make it 'environmentally friendly' and potentially useful for industrial applications.
