156304-06-2Relevant academic research and scientific papers
Microwave Mediated Synthesis and Analytical Method Development for the Estimation of Novel 1,4-Dihydropyridines in Bulk by RP-HPLC
Kaur, Anupreet,Kaur, Jaspreet,Bansal, Ranju
, p. 296 - 300 (2018)
The present work describes a rapid and green microwave mediated method for the synthesis and a simple and precise isocratic reverse phase HPLC method for the estimation of the biologically significant dihydropyridines. The conventional synthesis of these
[Fesipmim]Cl as highly efficient and reusable catalyst for solventless synthesis of dihydropyridine derivatives through Hantzsch reaction
Agrwal, Akansha,Kasana, Virendra
, (2020/06/01)
Abstract: In the present investigation, magnetic ferrite nanoparticles (ferrite NPs) were synthesized and coated with silica (ferrite?SiO2NPs) by using the sol-gel method. After that, silica propylmethylimidazolium chloride ionic liquid [Sipmim]Cl was prepared and linked with the above-prepared ferrite?SiO2NPs to synthesize ferrite silica propylmethylimidazolium chloride [Fesipmim]Cl catalyst. The formation of [Fesipmim]Cl catalyst was confirmed by Fourier-transform infrared (FT-IR) spectroscopy analysis. X-ray diffraction (XRD) analysis confirmed the structure of ferrite NPs and ferrite?SiO2 NPs. Transmission electron microscopy (TEM) evidenced the successful formation of ferrite NPs and ferrite?SiO2 NPs. Scanning electron microscopy (SEM) results revealed the change in morphology of ferrite NPs, ferrite?SiO2NPs and [Fesipmim]Cl. The magnetic properties of [Fesipmim]Cl catalyst were measured by vibrating sample magnetometer (VSM). The efficiency of the [Fesipmim]Cl catalyst was checked by using it for the synthesis of different derivatives of dihydropyridine through Hantzsch reaction via a three-component coupling reaction of substituted benzaldehydes, ethyl/ methyl acetoacetate and ammonium acetate. The formation and structures of all the synthesized compounds were confirmed by FT-IR, 1HNMR, 13C NMR spectral analyses. The reusability of the catalyst [Fesipmim]Cl was checked up to seven cycles and found to have excellent activity up to five cycles. Graphic abstract: [Figure not available: see fulltext.].
A New Type of Magnetically-Recoverable Heteropolyacid Nanocatalyst Supported on Zirconia-Encapsulated Fe3O4 Nanoparticles as a Stable and Strong Solid Acid for Multicomponent Reactions
Zolfagharinia, Somayeh,Kolvari, Eskandar,Koukabi, Nadiya
, p. 1551 - 1566 (2017/05/17)
Abstract: A novel highly efficient magnetically retrievable catalyst was developed by the immobilization of H3PW12O40 (20–60 wt%) on the surface of zirconia-encapsulated Fe3O4 nanoparticles. The prepared HPW supported on nano-Fe3O4@ZrO2 heterogeneous acid catalyst (or n-Fe3O4@ZrO2/HPW) was fully characterized by several physicochemical techniques such as: Fourier transform infrared spectroscopy (FT-IR), field emission scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, vibrating sample magnetometry and thermogravimetric analysis. The FT-IR spectroscopic data revealed that H3PW12O40 molecules on the nano-Fe3O4@ZrO2 support existed in the Keggin structure. The acidity of the catalyst was measured by the help of a potentiometric titration with n-butylamine. It was surprising that this very strong solid acid catalyst exhibited an excellent acid strength which was as a result of possessing a higher number of surface active sites compared to its homogeneous analogues. The catalytic activity of the as-prepared novel nano-Fe3O4@ZrO2/HPW was explored through the one-pot three-component synthesis of different 3,4-dihydropyrimidin-2(1H)-ones (i.e. Biginelli reaction) and 1,4-dihydropyridines (i.e. Hantzsh reaction) under solvent free condition. The sample of 40 wt% showed higher acidity and activity in the catalytic transformation. After the reaction, the catalyst/product isolation could be easily achieved with an external magnetic field and the catalyst could be easily recycled for at least five times without any decrease in its high catalytic activity. The excellent recyclability was attributed to the strong interaction between the hydroxyl groups of the nano-Fe3O4@ZrO2 support and the HPW species. Graphical Abstract: [Figure not available: see fulltext.].
Heterogeneous bimetallic ZnFe2O4nanopowder catalyzed synthesis of Hantzsch 1,4-dihydropyridines in water
Ravikumar Naik,Shivashankar
supporting information, p. 4046 - 4049 (2016/08/18)
The mixed metal oxide ZnFe2O4nanopowder, a dual Lewis acid–base combined catalyst is found to efficiently catalyze a multicomponent synthesis of 1,4-dihydropyridines from aldehydes, ethyl acetoacetate, and ammonium acetate in water. This procedure offers several advantages including high yields, short reaction times, a simple work-up procedure, and a benign eco-footprint. This method takes advantage of the fact that water, a green solvent is used in combination with ZnFe2O4nanoparticles as catalyst which can be easily recovered magnetically and reused for further runs.
Synthesis of hantzsch 1,4-dihydropyridines in a continuous flow microreactor
Gao, Peiyuan,Sun, Xuan,Lei, Ming,Zhang, Hong
, p. 755 - 761 (2017/04/10)
A simple and efficient synthesis of Hantzsch 1,4-dihydropyridines from the condensation of benzaldehydes with alkyl acetoacetates/benzoylacetate and aqueous ammonia in the absence of catalyst has been developed by using a continuous flow microreactor. Under optimized condition, various 1,4-dihydropyridines were obtained in 80-93% yield with high atom efficiency. Compared with using batch system, the present smooth procedure greatly accelerated the reaction due to the excellent mixing and mass transfer of reactant in micro flow system.
A Simple and Efficient One-pot Synthesis of 1,4-dihydropyridines Using Nano-WO3-supported Sulfonic Acid as an Heterogeneous Catalyst under Solvent-free Conditions
Bitaraf, Mehrnoosh,Amoozadeh, Ali,Otokesh, Somayeh
, p. 336 - 344 (2016/05/09)
Nano-tungsten trioxide-supported sulfonic acid (n-WSA) was found to be an effective heterogeneous catalyst for the one-pot reaction of aromatic aldehydes, β-dicarbonyl compounds and ammonium acetate to afford 1,4-dihydropyridine derivatives in good to excellent yields. The other main advantages of the present method are short reaction times, simple workup, ease in purification and environmentally benign methodology. The reaction conditions were optimized employing Response Surface Method technique (Central Composite Design (CCD)) which is economically considerable because of the minimum number of experiments required to evaluate the effects of multiple parameters on the response.
Ultrasound-mediated, uranyl nitrate hexahydrate-catalyzed synthesis of 1,4-dihydropyridines under mild conditions
Palakshi Reddy,Sarveswari,Vijayakumar
, p. 6877 - 6883 (2015/08/18)
Abstract Synthesis of 1,4-dihydropyridines by three-component condensation reaction of aldehyde, 1,3-dicarbonyl compounds, and ammonium acetate have been found to be efficiently catalyzed by uranyl nitrate hexahydrate [UO2(NO3)2 ·6H2O] at room temperature under ultrasound irradiation. This novel synthetic method offers the advantages of high yields, short reaction times, simplicity, and easy workup compared to the conventional methods reported in the literature.
Hybrid pharmacophore-based drug design, synthesis, and antiproliferative activity of 1,4-dihydropyridines-linked alkylating anticancer agents
Singh, Rajesh K.,Prasad,Bhardwaj
, p. 1534 - 1545 (2015/04/21)
Two series of novel substituted 1,4-dihydropyridine derivatives incorporating nitrogen mustard pharmacophore hybrids without spacer DHP-M (4a-4d) and with ethyl spacer DHP-L-M (8a-8g) were designed and synthesized. They were subjected to in silico ADME prediction study to check their drug-like properties and evaluated for their cytotoxicity against: A 549 (lung), COLO 205 (colon), U 87 (glioblastoma), and IMR-32 (neuroblastoma) human cancer cell lines in vitro using 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay against chlorambucil and docetaxel. Majority of the test compounds exhibited moderate to significant cytotoxic activity. The highest activity in all the investigated cancer cells was displayed by DHP-M (4a). This may be due to the less steric hindrance offered by 4a.
Alginic acid: A highly efficient renewable and heterogeneous biopolymeric catalyst for one-pot synthesis of the Hantzsch 1,4-dihydropyridines
Dekamin, Mohammad G.,Ilkhanizadeh, Siamand,Latifidoost, Zahra,Daemi, Hamed,Karimi, Zahra,Barikani, Mehdi
, p. 56658 - 56664 (2015/02/02)
Alginic acid, a naturally occurring polysaccharide, in its granular form and without any post-modification was found to be an efficient, environmentally benign, easily recoverable and low-cost catalyst for the clean and rapid synthesis of 1,4-dihydropiridine derivatives (DHPs) just based on its polysaccharide architecture. The Hantzsch pseudo-four-component reaction of ethyl or methyl acetoacetate, ammonium acetate and different aldehydes is catalyzed by alginic acid efficiently under mild conditions to afford the desired products in high to quantitative yields and clean reaction profiles. Avoiding the use of any transition metal, the use of a one-pot and multi-component procedure for the synthesis of DHPs, the reusability of the catalyst and operational simplicity are important features of this methodology.
Regioselective synthesis of novel 2-chloroquinoline derivatives of 1,4-dihydropyridines
Rajesh,Iniyavan,Sarveswari,Vijayakumar
, p. 1851 - 1866 (2014/05/06)
Highly regioselective reaction of some substituted 2,4-dichloroquinolines with symmetrical 1,4-dihydropyridines, leading to novel quinoline derivatives of DHPs, has been achieved in the presence of powdered K2CO 3, as a mild and efficient base, at moderate temperature. All the synthesized compounds were characterized by use of IR, NMR, and mass spectral data.
