1149-24-2

Usage

Uses

Used in Pharmaceutical Industry:
DIETHYL 2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLATE is used as an intermediate compound for the synthesis of various pharmaceutical products. Its unique chemical structure allows it to be a key component in the development of new drugs, particularly those targeting cardiovascular diseases, as Hantsch dihydropyridines are known for their vasodilatory properties.
Used in Chemical Research:
In the field of chemical research, DIETHYL 2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLATE serves as a valuable compound for studying the properties and reactions of Hantsch dihydropyridines and their derivatives. This helps researchers understand the underlying mechanisms and potential applications of these compounds in various chemical processes.
Used in Material Science:
DIETHYL 2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLATE may also find applications in material science, particularly in the development of new materials with specific properties. Its unique chemical structure could contribute to the creation of advanced materials with improved performance in various applications, such as electronics, coatings, or polymers.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 2, p. 214, 1943Tetrahedron, 28, p. 5911, 1972Tetrahedron Letters, 34, p. 623, 1993 DOI: 10.1016/S0040-4039(00)61635-0

InChI:InChI=1/C13H17NO4/c1-5-17-12(15)10-7-11(13(16)18-6-2)9(4)14-8(10)3/h7H,5-6H2,1-4H3

Upstream product

• 100-97-0 hexamethylenetetramine 
• 141-97-9 ethyl acetoacetate 
• 950-81-2 4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one 
• 626-34-6 ethyl 3-aminobut-2-enoate 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 1149-23-1 diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 61171-83-3 C₃₈H₃₀N₈ 
• 18998-44-2 α,α-Diphenyl-β-(2,4,6-tricyanophenyl)-hydrazyl 
• 57928-55-9 C₃₃H₂₀FN₇ 
• 57928-58-2 C₄₉H₅₃N₇S 
• 19262-50-1 1,3,5-(2,4,6-Tricyanobenzotriyl)tris(N¹,N¹-diphenylhydrazyl)-Triradikal 
• 61171-77-5 C₂₁H₁₀F₂N₅ 
• 18998-42-0 N_.N-Diphenyl-N'-(3.5-dichlor-2.4.6-tricyan-phenyl)-hydrazyl 
• 18998-43-1 2.4.6-Tricyan-5-chlorphenyl-1.3-bis-(N_.N-diphenylhydrazyl) 

Downstream Products

• 1721-13-7 ethyl 2,6-dimethylnicotinate 
• 2602-36-0 2,6-dimethyl-pyridine-3,5-dicarboxylic acid 
• 80812-55-1 ethyl 2-methyl-5-oxo-5,6-dihydro-1,6-naphthyridine-3-carboxylate 
• 74-85-1 ethene 
• 601490-73-7 2,7-diallyl-1,8-dioxo-4,5-bis(4-methoxyphenyliminomethyl)-1,2,7,8-tetrahydro-2,7,10-triaazaanthracene 
• 1026390-01-1 5-((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-2,6-dimethyl-nicotinic acid tert-butyl ester 

Relevant academic research and scientific papers

Reductive amination of aldehydes and ketones by a Hantzsch dihydropyridine using scandium triflate as a catalyst

Direct reductive amination of aldehydes and ketones was carried out using a Hantzsch dihydropyridine as a reducing agent in the presence of a catalytic amount of a Lewis acid.

Oxidative-aromatization of hantzsch ester 1,4-dihydropyridines by KBrO 3/Cocl2.6H2O under mild condition

KBrO3/CoCl2.6H2O system was used as an effective oxidizing agent for the oxidation of 1,4-dihydropyridines to the corresponding pyridine derivatives in refluxing CH3CN. The products were obtained in high to exce

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 novel, facile, simple and convenient oxidative aromatization of Hantzsch 1,4-dihydropyridines to pyridines using polymeric iodosobenzene with KBr

An easy, safe, effective and handy method for oxidative aromatization of Hantzsch 1,4-dihydropyridines catalyzed by hypervalent iodine (iodosobenzene) and potassium bromide to corresponding pyridine derivatives in high-yields and within short span of time was described. Dealkylation in case of 4-n-alkyl substituted 1,4-dihydropyridines was not obtained.

Histidine-Specific Peptide Modification via Visible-Light-Promoted C-H Alkylation

Histidine (His) carries a unique heteroaromatic imidazole side chain and plays irreplaceable functional roles in peptides and proteins. Existing strategies for site-selective histidine modification predominantly rely on the N-substitution reactions of the moderately nucleophilic imidazole group, which inherently suffers from the interferences from lysine and cysteine residues. Chemoselective modification of histidine remains one of the most difficult challenges in peptide chemistry. Herein, we report peptide modification via radical-mediated chemoselective C-H alkylation of histidine using C4-alkyl-1,4-dihydropyridine (DHP) reagents under visible-light-promoted conditions. The method exploits the electrophilic reactivity of the imidazole ring via a Minisci-type reaction pathway. This method exhibits an exceptionally broad scope for both peptides and DHP alkylation reagents. Its utility has been demonstrated in a series of important peptide drugs, complex natural products, and a small protein. Distinct from N-substitution reactions, the unsubstituted nitrogen groups of the modified imidazole ring are conserved in the C-H alkylated products.

Formation of pyridines from N-methylpyrimidinium iodide and enaminoesters

The reaction of N-methylpyrimidinium iodide with enaminoesters yiels a mixture of 3-ethoxycarbonyl-2-methylpyridine and 3,5-diethoxycarbonyl-2,6-dimethylpyridine.Mechanisms of the transformations of the pyrimidine ring found are suggested. - Keywords: N-methylpyridinium iodide; enaminoesters; ring transformation; pyridines; β-substituted.

The Aromatization of Hantzsch Dihydropyridines with Nitric Oxide (NO)

Hantzsch dihydropyridines were readily oxidized by nitric oxide to give corresponding pyridines in quantitative yields.This reaction system required no work-up procedure.In the presence of oxygen, it was possible to reduce nitric oxide to less than an equ

Diastereoselective Synthesis of Aryl C-Glycosides from Glycosyl Esters via C?O Bond Homolysis

C-aryl glycosyl compounds offer better in vivo stability relative to O- and N-glycoside analogues. C-aryl glycosides are extensively investigated as drug candidates and applied to chemical biology studies. Previously, C-aryl glycosides were derived from lactones, glycals, glycosyl stannanes, and halides, via methods displaying various limitations with respect to the scope, functional-group compatibility, and practicality. Challenges remain in the synthesis of C-aryl nucleosides and 2-deoxysugars from easily accessible carbohydrate precursors. Herein, we report a cross-coupling method to prepare C-aryl and heteroaryl glycosides, including nucleosides and 2-deoxysugars, from glycosyl esters and bromoarenes. Activation of the carbohydrate substrates leverages dihydropyridine (DHP) as an activating group followed by decarboxylation to generate a glycosyl radical via C?O bond homolysis. This strategy represents a new means to activate alcohols as a cross-coupling partner. The convenient preparation of glycosyl esters and their stability exemplifies the potential of this method in medicinal chemistry.

Photoactive electron donor-acceptor complex platform for Ni-mediated C(sp3)-C(sp2) bond formation

A dual photochemical/nickel-mediated decarboxylative strategy for the assembly of C(sp3)-C(sp2) linkages is disclosed. Under light irradiation at 390 nm, commercially available and inexpensive Hantzsch ester (HE) functions as a potent organic photoreductant to deliver catalytically active Ni(0) species through single-electron transfer (SET) manifolds. As part of its dual role, the Hantzsch ester effects a decarboxylative-based radical generation through electron donor-acceptor (EDA) complex activation. This homogeneous, net-reductive platform bypasses the need for exogenous photocatalysts, stoichiometric metal reductants, and additives. Under this cross-electrophile paradigm, the coupling of diverse C(sp3)-centered radical architectures (including primary, secondary, stabilized benzylic, α-oxy, and α-amino systems) with (hetero)aryl bromides has been accomplished. The protocol proceeds under mild reaction conditions in the presence of sensitive functional groups and pharmaceutically relevant cores.

Visible-light-driven external-photocatalyst-free alkylative carboxylation of alkenes with CO2

Herein, we report a novel protocol for visible-light-driven alkylative carboxylation of alkenes with CO2 in the absence of external photocatalyst. Under the irradiation of visible light, a variety of 4-alkyl-1,4-dihydropyridines (alkyl-DHPs) serve as not only alkyl radical precursors but also photoexcited reductants probably with the potential to reduce benzyl radicals. Several styrenes and acrylates are applicable in this reaction to give structurally diverse carboxylic acids in good to excellent yields. These reactions feature mild reaction conditions (1 atm of CO2, room temperature, visible light, photocatalyst- and transition metal-free), good functional group tolerance, easy scalability, as well as high regio-, and chemo-selectivity. Mechanistic investigations provide evidence that alkyl radical, benzyl radical and carbanion might be involved in this reaction, providing a novel strategy for CO2 utilization.[Figure not available: see fulltext.]