219701-24-3

Basic information

• Product Name: dimethyl 2,6-dimethyl-4-(2-thienyl)-3,5-pyridinedicarboxylate
• Synonyms: dimethyl 2,6-dimethyl-4-(2-thienyl)-3,5-pyridinedicarboxylate;2,6-dimethyl-4-(2-thienyl)pyridine-3,5-dicarboxylic acid dimethyl ester;2,6-Dimethyl-4-thiophen-2-yl-pyridine-3,5-dicarboxylic acid dimethyl ester;dimethyl 2,6-dimethyl-4-(2-thienyl)pyridine-3,5-dicarboxylate;dimethyl 2,6-dimethyl-4-thiophen-2-yl-pyridine-3,5-dicarboxylate;dimethyl 2,6-dimethyl-4-thiophen-2-ylpyridine-3,5-dicarboxylate;MFCD00203;MFCD00203547
• CAS NO: 219701-24-3
• Molecular Formula: C15H15NO4S
• Molecular Weight: 305.36
• Mol File: 219701-24-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: dimethyl 2,6-dimethyl-4-(2-thienyl)-3,5-pyridinedicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl 2,6-dimethyl-4-(2-thienyl)-3,5-pyridinedicarboxylate(219701-24-3)
• EPA Substance Registry System: dimethyl 2,6-dimethyl-4-(2-thienyl)-3,5-pyridinedicarboxylate(219701-24-3)

Safety Data

• Hazardous Substances Data: 219701-24-3(Hazardous Substances Data)

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 141-97-9 ethyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 14205-39-1 methyl 3-aminocrotonate 
• 162229-14-3 1,4-dihydro-2,6-dimethyl-4-(2-thienyl)-3,5-pyridinedicarboxylic acid bis-(1,1-methyl ester) 

Relevant articles and documents

Silica chromate as a novel oxidizing agent for the oxidation of 1,4-dihydropyridines

Silica chromate easily converts 1,4-dihydropyridines to their corresponding pyridines in the presence of NaHSO4·H2O and wet SiO2 in dichloromethane at room temperature in good to excellent yields. Copyright Taylor & Francis Group, LLC.

Graphite oxide-promoted one-pot synthesis and oxidative aromatization of Hantzsch 1,4-dihydropyridines

A new and efficient method for the one-pot synthesis of pyridine compounds using three-component Hantzsch synthesis in high yields using graphite oxide, a readily available and inexpensive material, as a mild and efficient agent is described. Graphical Abstract: [Figure not available: see fulltext.]

Remarkably fast and selective aromatization of Hantzsch esters with MoOCl4 and MoCl5: A chemical model for possible biologically relevant properties of molybdenum-containing enzymes

Mo(VI) and Mo(V) salts both react selectively with Hantzsch esters to produce substitute pyridines in good-to-excellent yield (75-99%). The remarkable reactivity and selectivity of MoOCl4 under reflux of acetonitrile and MoCl5 in dichloromethane at room temperature encouraged us to propose that molybdenum-containing enzymes (such as xanthine or aldehyde oxidase) also participate to some degree in the metabolism of 1,4-dihydropyridine drugs in the liver analogous to NADH in the respiratory chain.

A highly efficient biomimetic aromatization of Hantzsch-1,4-dihydropyridines with t-butylhydroperoxide, catalysed by iron(III) phthalocyanine chloride

Rapid aromatization of Hantzsch-1,4-DHPs with t-butylhydroperoxide catalysed by iron(III) phthalocyanine chloride is described. The reaction proceeds smoothly at room temperature within 1-35 min and the products of high purity were isolated in excellent yields. To explain the reactivity of this catalytical system plausible mechanism have been proposed to involve formation of high-valent oxoferryl species as in cytochrome P450 itself.

An efficient, metal-free, room temperature aromatization of Hantzsch-1,4-dihydropyridines with urea-hydrogen peroxide adduct, catalyzed by molecular iodine

A mild, highly efficient and metal-free synthetic method for aromatization of 1,4-dihydropyridines employing urea-hydrogen peroxide adduct as oxidant catalyzed by 20 mol % of molecular iodine was developed. The reaction was carried out in ethyl acetate at room temperature and the products were isolated in high to excellent yields. A plausible free-radical mechanism is proposed based on results obtained with derivatives having alkyl and aryl substituents in the 1,4-dihydropyridine ring.

Rapid, efficient, room temperature aromatization of Hantzsch-1,4-dihydropyridines with vanadium(V) salts: superiority of classical technique versus microwave promoted reaction

The aromatization of 1,4-dihydropyridines (1,4-DHPs) employing group 4 (Zr and Hf) and 5 (V, Nb, Ta) elements of periodic system has been studied. The reaction with VOCl3 in dichloromethane at room temperature afforded products, substituted pyridines, in high-to-excellent yield. For the first time, the formation of charge-transfer complexes (CTCs) has been evidenced in preorganization step between 1,4-DHP and oxidant before electron transfer. The CTC has been formed only in neutral solvents such as dichloromethane and is characterized by intensive coloration. The aromatization of 1,4-DHP with V2O5 in refluxing acetic acid has found to be superior over microwave promoted reaction in solventless media. The only reasonable explanation was found in polymeric structure of V2O5, which slowly transfer energy of microwaves needed for the activation of the reactants. The solvent polarity dependent oxidative dealkylation of 4-n-propyl-1,4-DHP has been discovered. Unexpectedly, the reaction in acetic acid afforded only 33% of dealkylated product compared to 91% obtained in dichloromethane under the same reaction conditions.

4-Phenyl-1,2,4-triazole-3,5-dione as a novel and reusable reagent for the aromatization of 1,4-dihydropyridines under mild conditions

4-Substituted 1,3,4-triazole-3,5-diones were used as effective and recyclable oxidizing agents for the oxidation of 1,4-dihydropyridines to the corresponding pyridine derivatives under mild conditions with good to excellent yields.

Microwave assisted combinatorial chemistry. Synthesis of substituted pyridines

A new highly efficient MICROCOS technology (Microwave-assisted Combinatorial Synthesis) for generating combinatorial libraries is described. The technology is applied to the high throughput, automated, one-step, parallel synthesis of diverse substituted pyridines using the Hantzsch synthesis. The advantages of microwave-assisted chemistry for combinatorial synthesis include a broad range of available chemistries, simple reaction setup and product recovery readily amenable to automation, extremely short reaction times, and high product yields.

Silica gel supported chromium trioxide: An effective reagent for aromatization of 4-alkyl/aryl-1,4-dihydropyridines

Oxidation of 4-alkyl/aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid diesters 1 has been carried out using silica gel supported CrO3 reagent. The supported reagent is prepared by co-grinding, CrO3 with silica gel in an agate mortar. In all the cases the corresponding aromatized product 2 is obtained in excellent yields (75-95 percent). Dealkylated product 3 obtained during oxidation of 4-isopropyl-1,4-dihydropyridine.