34148-68-0Relevant articles and documents
One-pot synthesis of 1,4-dihydropyridine derivatives using the Fe2ZnAl2O7 catalyzed Hantzsch three-component reaction
Zargarzadeh, Reza,Akbari Dilmaghani, Karim,Nikoo, Abbas
, p. 1310 - 1316 (2021/02/16)
A facile, low-cost, and effective one-pot method was developed for the synthesis of 1,4-dihydropyridine derivatives with high yields through the three-component reaction of ammonium acetate, ethyl acetoacetate, and aromatic aldehydes using Fe2ZnAl2O7 as catalyst. The reaction was conducted at 70–80°C temperature under solvent free conditions. The developed method had some great advantages, including safe and clean reaction conditions, high to excellent product yields, short reaction time, and a novel and powerful heterogeneous catalyst. The developed heterogeneous solid catalyst had high efficiency and reusability in one-pot multi-component syntheses such that it was easily reused four to five times without significant loss in efficiency and product yield. The catalyst was characterized by scanning Electron Microscopy (SEM)/energy-dispersive X-ray spectroscopy (EDS) and X-ray diffraction techniques. N2 sorption isotherms of the prepared nanocomposite exhibited surface area 2.1313E+01 m2/g and total pore volume of 3.0957E-02 cm3/g. Substituted dihydropyridine derivatives were characterized and confirmed using 1H NMR and 13C NMR, and elemental spectral data.
[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.].
Synergistic catalytic effect between ultrasound waves and pyrimidine-2,4-diamine-functionalized magnetic nanoparticles: Applied for synthesis of 1,4-dihydropyridine pharmaceutical derivatives
Taheri-Ledari, Reza,Rahimi, Jamal,Maleki, Ali
, (2019/09/03)
A convenient strategy for synthesis of the various derivatives of 1,4-dihydropyridine (1,4-DHP), as one of the most important pharmaceutical compounds, is presented in this study. For this purpose, firstly, magnetic iron oxide nanoparticles (Fe3O4 NPs) were fabricated and suitably coated by silica network (SiO2) and trimethoxy vinylsilane (TMVS). Then, their surfaces were well functionalized with pyrimidine-2,4-diamine (PDA) as the main active sites for catalyzing the synthesis reactions. In this regard, the performance of three different methods including reflux, microwave (MW) and ultrasound wave (USW) irradiations have been comparatively monitored via studying various analyses on the fabricated nanocatalyst (Fe3O4/SiO2-PDA). Concisely, high efficiency of the USW irradiation (in an ultrasound cleaning bath with a frequency of 50 kHz and power of 250 W/L) has been well proven through the investigation of the main factors such as excellent surface-functionalization, core/shell structure conservation, particle uniformity, close size distribution of the particles, and great inhibition of the particle aggregation. Then, the effectiveness of the USW irradiation as a promising co-catalyst agent has been clearly demonstrated in the 1,4-DHP synthesis reactions. It has been concluded that the USW could provide more appropriate conditions for activation of the catalytic sites of Fe3O4/SiO2-PDA NPs. However, high reaction yields (89%) have been obtained in the short reaction times (10 min) due to the substantial synergistic effect between the presented nanocatalyst and USW.
Silica-supported ceric ammonium nitrate (CAN): a simple, mild and solid-supported reagent for quickest oxidative aromatization of Hantzsch 1,4-dihydropyridines
Kumar, Parvin,Kadyan, Kulbir,Duhan, Meenakshi,Sindhu, Jayant,Hussain, Khalid,Lal, Sohan
, p. 1153 - 1162 (2019/04/25)
An efficient and environmentally benign methodology for the oxidative aromatization of 1,4-dihydropyridines to their corresponding pyridine derivatives is developed. The oxidative aromatization of 1,4-dihydropyridines was explored using silica-supported ceric ammonium nitrate as catalyst in CH3CN with or without sonication at room temperature. This supported catalyst acts as a more efficient oxidising reagent and offers several advantages over other reported reagents in terms of reaction time and yields. The supported reagent is found to be more efficient and selective when compared with its unsupported form. The Belousov–Zhabotinskii reaction was not observed in present reaction. The dealkylation observed in case of 4-n-alkyl/n-alkenyl with other oxidising agents is also not observed in the present case.
The efficient synthesis of Hantzsch 1,4-dihydropyridines via metal-free oxidative C–C coupling by HBr and DMSO
Rezaei, Narjes,Ranjbar, Parviz Rashidi
, p. 4102 - 4106 (2018/10/20)
A novel and efficient synthesis of Hantzsch 1,4-dihydropyridines through metal-free oxidative C–C coupling process was described. The reaction between benzylic alcohols, 1,3-dicarbonyl compounds and ammonium hydroxide in the presence of HBr in DMSO at 75 °C led to afford 1,4-dihydropyridine in excellent yields. This protocol introduces the use of benzyl alcohols instead of aldehydes as a new modification of the Hantzsch reaction.
Sulfated polyborate: An efficient and reusable catalyst for one pot synthesis of Hantzsch 1,4-dihydropyridines derivatives using ammonium carbonate under solvent free conditions
Rekunge, Deelip S.,Khatri, Chetan K.,Chaturbhuj, Ganesh U.
supporting information, p. 1240 - 1244 (2017/03/02)
A simple and efficient method for the synthesis of four-component 1,4-dihydropyridines of various aldehydes, β-ketoesters and ammonium carbonate catalyzed by sulfated polyborate with high yields under a solvent free condition at 90?°C is described. The key advantages of the present method are high yields, short reaction time, solvent free condition, easy workup, recyclability of catalyst and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards.
Benzyltrimethylammoniumfluoride Hydrate: An Efficient Catalyst for One-Pot Synthesis of Hantzsch 1,4-Dihydropyridines and Their Aromatization
Khaskel, Anamika,Barman, Pranjit
, p. 114 - 120 (2016/04/01)
An efficient, cost-effective and simple protocol has been developed for the synthesis of Hantzsch 1,4-dihydropyridines and their oxidation into pyridines using benzyltrimethylammonium fluoride hydrate as an excellent catalyst under solvent-free condition. All of the products synthesized by this method are characterized by various spectroscopic methods (IR, 1H NMR, 13C NMR, and DEPT).
Synthesis of diethyl 4-substituted-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates as a new series of inhibitors against yeast α-glucosidase
Niaz, Huma,Kashtoh, Hamdy,Khan, Jalaluddin A. J.,Khan, Ajmal,Wahab, Atia-Tul,Alam, Muhammad Tanveer,Khan, Khalid Mohammed,Perveen, Shahnaz,Choudhary, M. Iqbal
, p. 199 - 209 (2015/04/14)
1,4-Dihydropyridine-3,5-dicarboxylate derivatives (1-25) were synthesized in high yields via Hantzsch reaction and evaluated for their α-glucosidase inhibitory activity. Compounds 1, 2, 6-8, 11, 13-15, and 23-25 showed a potent inhibitory activity against yeast α-glucosidase with IC50 values in the range of 35.0-273.7 μM, when compared with the standard drug acarbose (IC50 = 937 ± 1.60 μM). Their structures were characterized by different spectroscopic techniques. The kinetics, selectivity, and toxicity studies on these compounds were also carried out. The kinetic studies on most active compounds 14 and 25 determined their modes of inhibition and dissociation constants Ki. Compound 14 was found to be a non-competitive inhibitor with Ki = 25.0 ± 0.06, while compound 25 was identified as a competitive inhibitor with Ki = 66.0 ± 0.07 μM.
L-Tyrosine loaded nanoparticles: An efficient catalyst for the synthesis of dicoumarols and Hantzsch 1,4-dihydropyridines
Khaskel, Anamika,Barman, Pranjit,Jana, Utpal
, p. 13366 - 13373 (2015/02/19)
Environmentally benign l-tyrosine loaded nanoparticles are fabricated and characterized by PCS, TEM, FT-IR and AFM studies. A novel straightforward green approach was applied for the synthesis of dicoumarols and Hantzsch 1,4-dihydropyridines using this catalyst. The structures and purity of these compounds were confirmed by FT-IR and NMR (1H, 13C and DEPT). The flexible and swelling properties of the polymer coating increase l-tyrosine dispersion and its high catalytic activity in organic reactions. This journal is
Urease: A highly biocompatible catalyst for switchable Biginelli reaction and synthesis of 1,4-dihydropyridines from the in situ formed ammonia
Tamaddon, Fatemeh,Ghazi, Somayeh
, p. 63 - 67 (2015/10/06)
Urease is a superior biocompatible catalyst for switching from the Biginelli reaction to urea-based synthesis of 1,4-dihydropyridines in water, where 100% switching occurs at 0.02 g/mL of enzyme. Hantzsch reaction with ammonium acetate (NH4OAc) is inefficiently catalyzed by urease (70%, 4 h), and heavy metal ions inhibit the urease-catalyzed reactions with urea or NH4OAc. Promotion of the urea-based Hantzsch reaction by urease and its inhibition with Hg2 + supports specificity of urease for in situ generation of ammonia, whereas the role of urease in further transformations is not so specific. The features of this enzymatic method are reusability, mild reaction conditions, biocompatibility, generality, and high yield of products.
