4408-96-2

Usage

InChI:InChI=1/C19H20N2O6/c1-5-26-18(22)15-11(3)20-12(4)16(19(23)27-6-2)17(15)13-8-7-9-14(10-13)21(24)25/h7-10H,5-6H2,1-4H3

Upstream product

• 21829-28-7 2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 39562-16-8 ethyl 2-(3-nitrophenylmethylene)-3-oxobutanoate 
• 141-97-9 ethyl acetoacetate 
• 99-61-6 3-nitro-benzaldehyde 
• 626-34-6 ethyl aminocrotonate 
• 619-25-0 3-Nitrobenzyl alcohol 

Downstream Products

• 89267-42-5 ethyl-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 

Relevant academic research and scientific papers

Catalytic aromatization of 1,4-dihydropyridines by radical cation salt prompted aerobic oxidation

Aromatization of Hantzch 1,4-dihydropyridines was achieved under radical cation salt induced conditions, in which triarylamine radical cation acts as an efficient catalyst to prompt the aerobic oxidation of 1,4-DHPs in a catalytic way.

Dimethyl 2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate, diethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, and diethyl 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

The crystal structure of diethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, C19H22N2O6 (FR7534), a member of the 1,4-dihydropyridine class of calcium blockers, and the crystal structures of diethyl 2,6-dimethyl-4-(3-nitrophenyl)-pryridine-3,5-dicarboxylate, C19H20N2O6, and dimethyl 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate, C17H16N2O6, decomposition products of FR7534 and dimethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, respectively, reveal that the decomposition products display conformational features associated with activity according to structure-activity relationship.

TEMPO supported amine functionalized magnetic titania: a magnetically recyclable catalyst for the aerobic oxidative synthesis of heterocyclic compounds

Abstract: The present protocol uncover a new strategy to synthesize highly efficient solid TEMPO based catalyst in which 4-oxo-TEMPO was covalently tethered to the surface of amine functionalized magnetic titania. The chemical nature and structure of the

Superparamagnetic core-shell metal–organic framework Fe3O4@Ni-MOF as efficient catalyst for oxidation of 1,4-dihydropyridines using hydrogen peroxide

A facile and efficient method was described for oxidation of some 3,5-diacyl or 3,5-diester 1,4-dihydropyridines using H2O2 in the presence of superparamagnetic core-shell metal–organic framework Fe3O4@Ni-MOF. The Fe3O4@Ni-MOF has been obtained by Step-by-Step method in which magnetic Fe3O4 magnetic nanoparticles were coated with Ni-MOF using a mercaptoacetic acid linker. The synthesized catalyst was characterized using thermogravimetric analysis, FT-IR spectroscopy, powder X-ray diffraction, field emission scanning electron microscopy and energy-dispersive X-ray analysis. The novel superparamagnetic core-shell metal–organic framework Fe3O4@Ni-MOF revealed high efficiency for oxidation of various 1,4-dihydropyridines using hydrogen peroxide. The Box–Behnken design matrix and the response surface method were applied to investigate the optimization of the reaction conditions. The conditions for optimal reaction yield and time were: amount of catalyst ≈17 mmol, temperature ≈78°C and amount of hydrogen peroxide ≈ 1 ml. A variety of 3,5-diacyl or 3,5-diester 1,4-dihydropyridines with different substituted functional groups have been converted to corresponding pyridines with good to excellent isolated yields using H2O2 and Fe3O4@Ni-MOF. The catalyst was reused up to five times for the oxidation of 1,4-dihydropyridines without a significant loss in catalytic activity. The short reaction times, simplicity of method, good to excellent yields and reusability of catalyst were some advantages of the proposed procedure.

One-pot synthesis of 3-hydroxy-2-oxindole-pyridine hybrids via Hantzsch ester formation, oxidative aromatization and sp3 C–H functionalization using FeWO4 nanoparticles as recyclable heterogeneous catalyst

Synthesis of poly-substituted 3-hydroxy-2-oxindole-pyridine hybrids is reported via sp3 C–H bond functionalization as key steps using FeWO4 nanoparticles as reusable heterogeneous catalyst. Formation of Hantzsch ester (DHP) followed by aromatization, and sp3 C–H bond functionalization was achieved using FeWO4 nanoparticles (20 mol%) at 80 °C. Temperature dependent reactivity was observed for mono aldol (at 80 °C) and bis aldol (at 120 °C) products. The catalyst was regenerated and reused up to 6 cycles without losing catalytic activity. The FeWO4 nanoparticles were also used for oxidative aromatization of different DHP derivatives and for the sp3 C–H functionalization of 2-methyl pyridine.

Hantzsch Reaction Starting Directly from Alcohols through a Tandem Oxidation Process

A Br?nsted acidic ionic liquid, 3-(N,N-dimethyldodecylammonium) propanesulfonic acid hydrogen sulphate ([DDPA][HSO4]), has been successfully applied to catalyze sequential oxidation of aromatic alcohols with NaNO3 followed by their c

Benzyltrimethylammoniumfluoride Hydrate: An Efficient Catalyst for One-Pot Synthesis of Hantzsch 1,4-Dihydropyridines and Their Aromatization

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).

Photoinduced Aromatization of Dihydropyridines

The combination of tris(bipyridine)ruthenium(II)/visible light/air is found to be effective for the aromatization of many dihydropyridines. A low catalyst loading of just 0.02 mol% is required.

A new oxidation system for the oxidation of Hantzsch-1,4-dihydropyridines and polyhydroquinoline derivatives under mild conditions

A new oxidation system (Na2S2O4/TBHP) to prepare pyridine derivatives has been developed by the oxidation of 1,4-dihydropyridine derivatives and polyhydroquinoline derivatives in good to excellent yields. The procedures of the reaction were green, convenient, mild and easy work-up.

Application of silica vanadic acid [SiO2-VO(OH)2] as a heterogeneous and recyclable catalyst for oxidative aromatization of Hantzsch 1,4-dihydropyridines at room temperature

A simple method for the oxidative aromatization of Hantzsch 1,4-dihydropyridines to the corresponding pyridines is described using hydrogen peroxide as green oxidant and silica vanadic acid as catalyst in acetonitrile at room temperature. The catalyst can