1149-23-1

Usage

Uses

Used in Antimicrobial Applications:
Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate is used as an antimicrobial agent for its demonstrated effectiveness against various microorganisms, making it a valuable compound in the development of new antimicrobial treatments and products.
Used in Chemical Synthesis:
Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate is used as a hydrogen source in organocatalytic reductive amination and conjugate reduction. Its role in these processes is crucial for the synthesis of various complex organic molecules, contributing to the advancement of chemical research and development.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate is used as a key intermediate in the synthesis of certain drugs, particularly those belonging to the dihydropyridine class. Its unique chemical properties make it a valuable component in the development of new medications with potential therapeutic applications.
Used in Material Science:
Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate may also find applications in material science, where its chemical properties could be harnessed to create novel materials with specific characteristics, such as improved stability or enhanced reactivity in certain conditions.

InChI:InChI=1/C13H19NO4/c1-5-17-12(15)10-7-11(13(16)18-6-2)9(4)14-8(10)3/h14H,5-7H2,1-4H3

Upstream product

• 50-00-0 formaldehyd 
• 141-97-9 ethyl acetoacetate 
• 626-34-6 ethyl aminocrotonate 
• 67079-26-9 diethyl 2,4-diacetylpentanedioate 
• 77287-34-4 formamide 
• 14558-49-7 tetrahydro-1,3-oxazine 
• 626-34-6 ethyl 3-aminobut-2-enoate 
• 20503-92-8 3-phenyl-oxazolidine 
• 64-17-5 ethanol 
• 75926-31-7 2,6-Dimethyl-3,5-bis(ethylthiocarbonyl)-1,4-dihydropyridine 
• 57-13-6 urea 
• 7664-41-7 ammonia 
• 5409-57-4 2,4-diacetyl-3-methyl-glutaric acid diethyl ester 
• 122-78-1 phenylacetaldehyde 

Downstream Products

• 849585-22-4 LACTIC ACID 
• 1721-13-7 ethyl 2,6-dimethylnicotinate 
• 2602-36-0 2,6-dimethyl-pyridine-3,5-dicarboxylic acid 
• 1149-24-2 2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 5770-42-3 1,3-dimethyl-6-methylamino-1H-pyrimidine-2,4-dione 
• 105167-94-0 1,3,7,8a,9-Pentamethyl-2,4-dioxo-1,3,4,5,8,8a,9,10-octahydro-2H-1,3,8,9-tetraaza-anthracene-6,10a-dicarboxylic acid diethyl ester 
• 61360-76-7 2,4-Bis-(N',N'-diphenyl-hydrazino)-6-piperidin-1-yl-benzene-1,3,5-tricarbonitrile 
• 19197-83-2 α,α-Diphenyl-β-(2,4,6-tricyanophenyl)-hydrazin 
• 57928-51-5 1,3-Bis-(N',N'-diphenyl-hydrazino)-5-fluor-2,4,6-tricyan-benzol 
• 57928-54-8 1,3-Bis-(N',N'-diphenyl-hydrazino)-5-hexadecylthio-2,4,6-tricyan-benzol 
• 20329-31-1 1,3,5-Tris-(N',N'-diphenyl-hydrazino)-2,4,6-tricyan-benzol 
• 130452-67-4 C₂₃H₃₁N₂O₅ 
• 61171-75-3 2-(N',N'-Diphenyl-hydrazino)-4,6-difluoro-benzene-1,3,5-tricarbonitrile 

Relevant academic research and scientific papers

Hydrogen-bonded molecular capsules: Probing the role of water molecules in capsule formation in modified cyclotricatechylene

Two new pyridine moiety-appended cavitands, CTC(Py)2(OH)2 and CTC(Py)3, were synthesized and characterized. The solid state structures of both cavitands were studied by single crystal X-ray diffraction. CTC(Py)2(OH)2 resulted in a hydrogen-bonded dimeric molecular capsule, entrapping two molecules of DMSO and intervening water molecules that formed hydrogen bonding to DMSO and CTC(Py)2(OH)2. When crystallized in the absence of water, it forms a 2D polymer by hydrogen bonding of pyridine nitrogen and phenolic hydrogen atoms. CTC(Py)3 forms no such capsule.

Ferric chloride hexahydrate: A convenient reagent for the oxidation of hantzsch 1,4-dihydropyridines

A general and practical route for the moderate yield oxidative conversion of readily accessible 1,4-dihydropyridines (1,4-DHPs) to the corresponding pyridines was described using a relatively benign oxidant, i.e. ferric chloride hexahydrate (FeCl3·6H2O). The reaction was carried out under mild and convenient condition. However, oxidation of 4-isopropyl-1,4-DHP 1b with FeCl3·6H2O afforded the dealkylated pyridine 2a.

Synthesis of the pyridine hydrazones as metal-free artificial nucleases

In this report, four pyridine hydrazones containing anthracene and triphenylamine as a new type of metal-free nucleases were synthesized. Results indicate that the conjugates can cleave the plasmid DNA to Form II or Form III under physiological conditions via hydrolytic pathway.

Oxidative aromatization of hantzsch 1,4-dihydropyridines by H 2O2/V2o5 at room temperature

A mild and highly efficient synthetic method was developed for the aromatization of 1,4-dihydropyridines employing H2O2 and 5mol% of V2O5. The reactions were carried out in CH 3CN to give pyridine compounds in excellent yields. Copyright Taylor & Francis Group, LLC.

Rhodium-Catalyzed Diastereo- And Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines

A highly selective rhodium-catalyzed tandem spirocyclization/reduction of 3-allenylindoles is reported. By employing a Hantzsch ester as reductant, vinylic spiroindolines are obtained in excellent yields as well as diastereo- and enantioselectivity. In addition, the reaction's synthetic utility is highlighted by broad functional group compatibility and exemplified by a gram scale reaction with subsequent assorted transformations.

Slow generation of hydrogen sulfide from sulfane sulfurs and NADH models

Here we report the model studies of the reactions between NADH models (using HEH and BNAH) and sulfane sulfurs (using polysulfides). Such reactions could lead to the oxidation of NADH models and the production of hydrogen sulfide (H2S). Kinetics of the reaction between BNAH and elemental sulfur S8were determined in ethanol and the second-order rate constant was found to be 0.074?M?1?min?1(at 37?°C) suggesting this is a slow process.

Formic acid disproportionation into formaldehyde triggered by vanadium complexes with iridium catalysis under mild conditions inN-methylation

Formaldehyde (CH2O) has been used as a key platform reagent in the chemical industry for many decades. Currently, the industrial production of CH2O mainly depends on fossil resources, involving a highly energetic three-step process (200-1100 °C). Herein, we describe renewable formic acid (HCO2H) disproportionation into CH2O triggered by vanadium complexes with iridium catalysis under mild conditions at 30-50 °C inN-methylation. The gram-scale application ofin situgenerated CH2O by HCO2H disproportionation is demonstrated.

Evaluation of Organic Hydride Donors as Reagents for the Reduction of Carbon Dioxide and Metal-Bound Formates

A variety of organic hydride donors (OHDs) have been tested as reagents for the transfer of hydride to iron formato complexes in the activation and reduction of carbon dioxide. Theoretical calculations show that the selection of OHD and solvent is crucial when planning systems involving OHD cooperativity. Strong consideration is given to the likelihood that metal centers may deactivate formate to hydride attack, since, in general, the formate group has more resonance stabilization energy when complexed to a metal center compared to an organoformate or formic acid. It is experimentally demonstrated that 1,2-dihydropyridine is not a competent reducing agent for carbon dioxide.

Late-Stage C-H Alkylation of Heterocycles and 1,4-Quinones via Oxidative Homolysis of 1,4-Dihydropyridines

Under oxidative conditions, 1,4-dihydropyridines (DHPs) undergo a homolytic cleavage, forming exclusively a Csp3-centered radical that can engage in the C-H alkylation of heterocyclic bases and 1,4-quinones. DHPs are readily prepared from aldehydes, and considering that aldehydes normally require harsh reaction conditions to take part in such transformations, with mixtures of alkylated and acylated products often being obtained, this net decarbonylative alkylation approach becomes particularly useful. The present method takes place under mild reaction conditions and requires only persulfate as a stoichiometric oxidant, making the procedure suitable for the late-stage C-H alkylation of complex molecules. Notably, structurally complex pharmaceutical agents could be functionalized or prepared with this protocol, such as the antimalarial Atovaquone and antitheilerial Parvaquone, thus evidencing its applicability. Mechanistic studies revealed a likely radical chain process via the formation of a dearomatized intermediate, providing a deeper understanding of the factors governing the reactivity of these radical forebears.

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.