1721-13-7

Usage

Uses

Used in Pharmaceutical Industry:
2,6-DIMETHYL-NICOTINIC ACID ETHYL ESTER is used as a building block for the synthesis of various drug molecules, primarily for the creation of antifungal agents and antihypertensive drugs. Its structural properties allow for the development of medications that target specific conditions effectively.
Used in Neurodegenerative Disease Treatment:
2,6-DIMETHYL-NICOTINIC ACID ETHYL ESTER is studied for its potential use in treating neurodegenerative diseases due to its inherent biological activity, which may offer therapeutic benefits in managing such conditions.
Used in Inflammatory Condition Treatment:
Additionally, it has been investigated for its potential role in treating inflammatory conditions, suggesting that its chemical structure may contribute to reducing inflammation and associated symptoms.

InChI:InChI=1/C10H13NO2/c1-4-13-10(12)9-6-5-7(2)11-8(9)3/h5-6H,4H2,1-3H3

Upstream product

• 70271-80-6 ethyl 4-chloro-2,6-dimethylnicotinate 
• 1563-45-7 (2Z,3E)-ethyl 2-(1-aminoethylidene)-5-oxohex-3-enoate 
• 1149-23-1 diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 1149-24-2 2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester 
• 5744-65-0 1,1,3,3-tetramethoxy-butane 
• 141-97-9 ethyl acetoacetate 
• 626-34-6 ethyl 3-aminobut-2-enoate 
• 5436-21-5 acetylacetaldehyde dimethyl acetal 
• 4643-20-3 (E)-4-chloro-3-buten-2-one 
• 593-67-9 vinylamine 
• 75-07-0 acetaldehyde 
• 41867-20-3 ethyl (E)-3-aminobut-2-enoate 
• 480453-20-1 (4E)-2-amino-3-ethoxycarbonylhepta-2,4-dien-6-one 
• 5930-98-3 4-trimethylsilyl-3-butyn-2-one 

Downstream Products

• 109812-11-5 2-methyl-6-(3-nitro-trans-styryl)-nicotinic acid ethyl ester 
• 109471-60-5 2-methyl-6-trans-styryl-nicotinic acid ethyl ester 
• 102452-11-9 (+/-)-7-phenyl-2-trans-styryl-7,8-dihydro-pyrano[4,3-b]pyridin-5-one 
• 1721-25-1 1-(2,6-dimethylpyridin-3-yl)ethan-1-one 
• 582303-10-4 (2,6-dimethylpyridin-3-yl)methanol 
• 5860-71-9 2,6-dimethylpyridine-3-carboxylic acid 
• 672325-49-4 (2,6-dimethylpyridin-3-yl)methanamine 
• 1462-84-6 2,3,6-trimethylpyridine 
• 108-48-5 2,6-dimethylpyridine 
• 118420-52-3 (E)-N-[4-(4-Benzhydryl-piperazin-1-yl)-butyl]-3-(2,6-dimethyl-pyridin-3-yl)-acrylamide 
• 650141-20-1 2,6-dimethylpyridine-3-carboxaldehyde 
• 113056-89-6 2,6-bis-(3-nitro-trans-styryl)-nicotinic acid 
• 108619-14-3 2-methyl-6-(3-nitro-trans-styryl)-nicotinic acid 
• 101876-19-1 6-((αRS,βSR)-α,β-dibromo-phenethyl)-2-methyl-nicotinic acid ethyl ester 

Relevant academic research and scientific papers

A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines

The one-pot three-component condensation of a β-ketoester, ammonia and an alkynone in the presence of a Bronsted or Lewis acid or Amberlyst 15 ion exchange resin provided 2,3,6-trisubstituted or 2,3,4,6-tetrasubstituted pyridines directly in good yield and with total regiocontrol.

Marriage of Peroxides and Nitrogen Heterocycles: Selective Three-Component Assembly, Peroxide-Preserving Rearrangement, and Stereoelectronic Source of Unusual Stability of Bridged Azaozonides

Stable bridged azaozonides can be selectively assembled via a catalyst-free three-component condensation of 1,5-diketones, hydrogen peroxide, and an NH-group source such as aqueous ammonia or ammonium salts. This procedure is scalable and can produce gram quantities of bicyclic stereochemically rich heterocycles. The new azaozonides are thermally stable and can be stored at room temperature for several months without decomposition and for at least 1 year at-10 °C. The chemical stability of azaozonides was explored for their subsequent selective transformations including the first example of an aminoperoxide rearrangement that preserves the peroxide group. The amino group in aminoperoxides has remarkably low nucleophilicity and does not participate in the usual amine alkylation and acylation reactions. These observations and the 15 pKa units decrease in basicity in comparison with a typical dialkyl amine are attributed to the strong hyperconjugative nN→σ*C-O interaction with the two antiperiplanar C-O bonds. Due to the weakness of the complementary nO→σ*C-N donation from the peroxide oxygens (a consequence of inverse α-effect ), this interaction depletes electron density from the NH moiety, protects it from oxidation, and makes it similar in properties to an amide.

Synthesis of pyridines and pyrido[2,3-d]pyrimidines by the Lewis acid catalysed Bohlmann-Rahtz heteroannulation reaction

Lewis acids catalyse the Bohlmann-Rahtz heteroannulation reaction to generate highly functionalised pyridines from enamino esters and alkynones in a single synthetic step. Of the catalysts studied, ytterbium(III) trifluoromethanesulfonate and zinc(II) bromide are the two most efficient for the synthesis of pyridines and pyrido[2,3-d]pyrimidines, from ethyl β-aminocrotonate or 2,6-di-aminopyrimidin-4-one respectively, in up to 94% yield.

Tailor-made synthesis of fully alkylated/arylated nicotinates by FeCl3-mediated condensation of enamino esters with enones

A new method for synthesizing polyalkylated/arylated nicotinates is established using a condensation of enamino esters with enones in the presence of FeCl3. This method facilitates the introduction of alkyl or aryl groups at any position on demand, which has not been achieved by other procedures.

Bohlmann-Rahtz cyclodehydration of aminodienones to pyridines using N-iodosuccinimide

Cyclodehydration of Bohlmann-Rahtz aminodienone intermediates using N-iodosuccinimide as a Lewis acid proceeds at low temperature under very mild conditions to give the corresponding 2, 3,6-trisubstituted pyridines in high yield and with total regiocontrol.

Continuous flow processing from microreactors to mesoscale: The Bohlmann-Rahtz cyclodehydration reaction

The cyclodehydration of a number of Bohlmann-Rahtz aminodienones exemplifies the use of continuous flow processing to transfer operations from commercial microreactors and microwave batch reactors to mesoscale production using different technology platforms, including a microwave flow reactor.

One-pot multistep Bohlmann-Rahtz heteroannulation reactions: Synthesis of dimethyl sulfomycinamate

(Chemical Equation Presented) The synthesis of dimethyl sulfomycinamate, the acidic methanolysis product of the sulfomycin family of thiopeptide antibiotics, from methyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is achieved in a 2,3,6-trisubstituted pyridine synthesis that proceeds with total regiocontrol in 13 steps by the Bohlmann-Rahtz heteroannulation of a 1-(oxazol-4-yl)enamine or in 12 steps and 9% yield by three-component cyclocondensation with N-[3-oxo-3-(oxazol-4-yl)propanoyl]serine and ammonia in ethanol.

Iodine-catalysed Bohlmann-Rahtz cyclodehydration reactions

The cyclodehydration of Bohlmann-Rahtz aminodienones is catalysed by iodine in ethanol at room temperature to give 2,3,6-trisubstituted pyridines in excellent yield, with total regiocontrol and without the need for chromatographic purification.

Alpha-substituted arylalkyl phosphonate derivatives

The present invention relates to novel α-substituted arylalkylphosphonate derivatives and their uses for lowering plasma levels of apo (a), Lp(a), apo B, apo B associated lipoproteins (low density lipoproteins and very low density lipoproteins) and for lo

A new mild method for the one-pot synthesis of pyridines

Polysubstituted pyridines are prepared in good yield and with total regiocontrol by the one-pot reaction of an alkynone, 1,3-dicarbonyl compound and ammonium acetate in alcoholic solvents. This new three-component heteroannulation reaction proceeds under mild conditions in the absence of an additional acid catalyst and has been used in the synthesis of dimethyl sulfomycinamate, the acidic methanolysis degradation product of the sulfomycin family of thiopeptide antibiotics.