58395-00-9

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 631-61-8 ammonium acetate 
• 141-97-9 ethyl acetoacetate 
• 140-75-0 para-fluorobenzylamine 

Downstream Products

• 1262983-77-6 1-(2-(phthalimido-N-oxy)ethyl)-2,6-dimethyl-N₃,N₅-bis(4-oxo-2-phenylquinazolin-3(4H)-yl)-4-(4-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxamide 
• 1262983-73-2 2,6-dimethyl-N₃,N₅-bis(4-oxo-2-phenylquinazolin-3(4H)-yl)-4-(4-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxamide 
• 1262983-67-4 4-(4-fluorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbohydrazide 
• 137887-39-9 diethyl 1,2,6-trimethyl-4-(4-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 

Relevant academic research and scientific papers

Solvent free, environment benign synthesis of 1,4-dihydropyridines and polyhydroquinolines by using heterogeneous Zn/MCM-41 catalyst

Heterogeneous catalysis has been utilized in number of efficient reactions with higher selectivity of the product, more stable, reusable and easy for separation as compared to homogeneous catalysts. Generally, heterogeneous catalysts are prepared by using mesoporous materials, microporous materials, metal oxides and metal organic framework. The mesoporous materials have small particle size and high surface area as compared to the microporous materials. The adsorbent mesoporous materials have highly efficient for the therapeutic applications in chemistry hence it has best as compared to other heterogeneous materials. Herein, we have reported synthesis of 1,4-dihydropyridines and polyhydroquinolines at solvent free and environmental benign condition in the presence of Zn/MCM-41 catalyst. The present protocol gives excellent yield (89–96%) of the product within short reaction time by easy work up procedure and no need of further purification of product. The catalyst was characterized by XRD diffractometer, SEM, EDAX, TGA-DTA, BET surface area analysis and FT-IR Spectroscopy. The synthesized organic compounds were characterized by FT-IR, 1H NMR, 13C NMR, LC–MS spectrometry. Graphical abstract: [Figure not available: see fulltext.]

Sulfonamide-functionalized covalent organic framework (COF-SO3H): an efficient heterogeneous acidic catalyst for the one-pot preparation of polyhydroquinoline and 1,4-dihydropyridine derivatives

Herein, we report the sulfonamide-functionalized covalent organic framework (COF-SO3H) prepared from melamine and terephthalaldehyde and subsequent sulfonation, as an acidic porous catalyst for the one-pot preparation of polyhydroquinoline and

Synthesis, Crystal structure, DFT calculations and antimicrobial activity of 4-(4-fluoro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

The title compound was synthesized and confirmed by FT-IR, 1H, 13C NMR analysis. The molecular structure of the compound was precisely determined by Single Crystal X-ray Diffraction (SC-XRD) analysis. The crystalized compound shows P

One-Pot Synthesis of 1,4-Dihydropyridine Derivatives and Their X-Ray Crystal Structures: Role of Fluorine in Weak Interactions

1,4-dihydropyridines, namely diethyl 4-(4-fluorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (1a), diethyl 2,6-dimethyl-4-(3,4,5-trimethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate(1b), and diethyl 4-(3,4-dimethoxyphenyl)-2,6-dihydroxy-2

Trinuclear cis-dioxidomolybdenum(VI) complexes of compartmental C3 symmetric ligands: Synthesis, characterization, DFT study and catalytic application for hydropyridines (Hps) via the Hantzsch reaction

Trinuclear cis-dioxidomolybdenum(VI) complexes of the type [{MoVIO2(MeOH)}3L1-7] (1–7) have been synthesized using tris(H2ONO) donor ligands [H6L1-7 (I–VII)] assembled from benzene-1,3,5-tricarbohydrazide (bthz) and the corresponding salicylaldehyde (sal). All the ligands and the complexes were characterized by numerous techniques, such as FT-IR, UV–visible, NMR (1H and 13C) spectroscopy, electrochemical study, elemental analysis, thermogravimetric study and single crystal X-ray diffraction of the ligand III and complexes 1 and 5. In the presence of H2O2 as an oxidant, these complexes show excellent catalytic potential towards the one-pot three-components [ethyl acetoacetate, benzaldehyde (or its derivatives) and ammonium acetate] dynamic covalent assembly in the Hantzsch reaction. Under solvent free conditions, as high as 98% conversion along with 100% selectivity towards diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate (1,4-DHP) has been achieved in 1 h. Although solvents do not improve the conversion, they do influence the selectivity of the products. With the elapse of time, the conversion of dihydropyridine to the diethyl 2,6-dimethyl-4-phenylpyridine-3,5-dicarboxylate derivative occurs and completes in ca. 10 h with a distinct color change, showing the importance of the catalysts. Efforts have been made to provide suitable reaction pathways for the catalytic reaction based on spectroscopic and density functional theory studies.

MIL-101-SO3H metal-organic framework as a Br?nsted acid catalyst in Hantzsch reaction: An efficient and sustainable methodology for one-pot synthesis of 1,4-dihydropyridine

A straightforward and efficient methodology for the one-pot multicomponent synthesis of 1,4-dihydropyridine has been developed using MIL-101-SO3H metal-organic framework as a solid Br?nsted acid. The presence of the uniformly distributed Br?nsted acidic sulfonic acid sites throughout the framework and the high stability bestow the catalyst with excellent reactivity towards the synthesis of 1,4-dihydropyridine under simple reaction conditions using renewable ethanol as the solvent. The present methodology tolerates various functional groups and allows the synthesis of 1,4-dihydropyridine derivatives in good to excellent yields through Hantzsch reaction. The developed methodology proceeds under mild conditions, avoids corrosive reagents and special reaction conditions, and is amenable to gram scale synthesis. The sustainable nature of the catalyst was proved by the easy recovery and the reusability of the catalyst, as it was reused several times without loss in activity, which was confirmed from the FTIR, PXRD and SEM analyses of the reused catalyst.

Synergistic catalytic effect between ultrasound waves and pyrimidine-2,4-diamine-functionalized magnetic nanoparticles: Applied for synthesis of 1,4-dihydropyridine pharmaceutical derivatives

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.

Metal free biomimetic deaminative direct C-C coupling of unprotected primary amines with active methylene compounds

An unprecedented direct C-C coupling reaction of unprotected primary amines with active methylene compounds is reported. The reaction involves a biomimetic deamination of amines which was achieved under conditions free of metallic reagents and strong oxidizing agents. A wide range of primary amines was reacted with different active methylene compounds to provide structurally diverse trisubstituted alkenes and dihydropyridines. A kinetic study revealed an activation barrier of 10.1 kcal mol-1 for the conversion of a key intermediate of the reaction.

From Zn(II) to Cu(II) framework via single-crystal to single-crystal metathesis with superior gas uptake and heterogeneous catalytic properties

In this work, a Zn(II) framework, {[Zn2(L)4(H2O)4]·(7DMF)(7H2O)}n (1Zn), has been synthesized using a bent tetracarboxylic acid ligand (H4L). The structure of 1Zn contains [Zn2(COO)4] paddle-wheel secondary building units with axial sites occupied by water molecules. Interestingly, the isostructural Cu(II) framework {[Cu2(L)4(H2O)4]·(7DMF)(7H2O)}n (1Cu) has been obtained via single-crystal to single-crystal metathesis reaction. The activated 1Cu (denoted as a1Cu; a stands for activated) has open coordination sites. This species showed enhanced CO2 adsorption and heterogeneous catalytic properties for the Hantzsch coupling reaction involving condensation of an aldehyde with ethyl acetoacetate and ammonium acetate to produce 1,4-dihydropyridines, and three-component coupling of amines, aldehydes and alkynes to generate propargylic amines with high efficiency.

Facile template-free route to fabricate core–shell Fe3O4@PANI-SO3H urchin-like nanoparticles as reusable catalyst for Hantzsch reaction: change morphology upon sulfonation

Abstract: This paper describes a novel and effective approach to fabricate the core–shell Fe3O4@PANI-SO3H urchin-like morphology in a self-assembly method as nano-magnetic solid acid catalyst. The Fe3O4@PANI microspheres were synthesized via an in situ surface polymerization of aniline monomer in an acidic condition, using ammonium persulfate as the oxidant. It was found that upon sulfonation of polyaniline (PANI), the morphology changes to morphology similar to urchin confirming the transmission electron microscopy and field emission scanning electron microscopy results. The as-prepared solid acid catalyst was also carefully analyzed by energy-dispersive X-ray spectroscopy, Fourier transform infrared spectroscopy, X-ray diffraction, thermogravimetric analysis and vibrating sample magnetometry. This new magnetic core–shell material was shown to have high catalytic performance for one–pot synthesis of 1,4-dihydropyridine derivatives. In addition, the catalyst can be easily separated using an external magnet. Recyclability and reusability for several runs, facile accessibility, and simple handling are the merits of this magnetic-heterogeneous acid catalyst. Graphical Abstract: [Figure not available: see fulltext.].