4685-10-3

Usage

Uses

Used in Pharmaceutical Industry:
3-(methoxycarbonyl)-1-methylpyridinium iodide is used as a reactant in the synthesis of quaternary ammonium salts for the development of pharmaceutical products. Its role in the synthesis process contributes to the creation of various medicinal compounds.
Used in Agrochemical Industry:
3-(methoxycarbonyl)-1-methylpyridinium iodide also finds application in the agrochemical sector, where it is utilized as a reactant in the synthesis of quaternary ammonium salts. These salts are essential in the development of agrochemical products, such as pesticides and herbicides, to enhance crop protection and yield.
Used in Research and Development:
3-(methoxycarbonyl)-1-methylpyridinium iodide is employed as a reactant in the research and development of new synthetic methods. Its versatility in organic synthesis allows scientists to explore innovative approaches and create novel compounds for various applications.

Upstream product

• 120-72-9 indole 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 74-88-4 methyl iodide 
• 59-67-6 nicotinic acid 

Downstream Products

• 1690-72-8 dihydroarecoline 
• 63-75-2 arecoline 
• 7680-69-5 1-methyl-3-(carbomethoxy)pyridinium chloride 
• 27531-47-1 1-methyl-6-phenyl-1,6-dihydro-pyridine-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Light-Promoted Dearomative Cross-Coupling of Heteroarenium Salts and Aryl Iodides via Nickel Catalysis

Partially saturated nitrogen heterocycles are versatile building blocks for the preparation of other nitrogen heterocycles. For example, dihydropyridines can be converted to pyridines, tetrahydropyridines, and piperidines through oxidation, reduction, and functionalization reactions, respectively. Dearomatization of heteroarenes is an attractive approach for the synthesis of partially saturated heterocycles such as dihydropyridines due to the wide availability of heteroarenes. Significant research efforts have been dedicated to the addition of nucleophiles to various heteroarenium salts in this direction using organoboron or organometallic reagents. The availability of organoboron and organometallic coupling partners has been an important limitation to this chemistry. Direct coupling of electrophiles with heteroareniums could significantly improve the scope of these dearomatization reactions due to the wider availability of electrophiles compared to nucleophiles such as organoboron and organometallic reagents. Herein, we report the coupling of aryl iodides with pyridinium and related heteroarenium salts catalyzed by Ni/bpp and an Ir photocatalyst using Zn as a terminal reductant. This methodology tolerates a wide range of functional groups and allows the coupling of aryl and heteroaryl iodides, thus significantly expanding the scope of nitrogen heterocycle scaffolds that could be prepared through dearomatization of heteroarenes. The reaction products have been further functionalized to prepare various nitrogen heterocycles. Initial mechanistic studies indicate that the reaction described herein goes through a unique mechanism involving dimers of dihydroheteroarenes.

A predictive model for additions to: N -alkyl pyridiniums

Disclosed in this communication is a thorough study on the dearomative addition of organomagnesium nucleophiles to N-alkyl pyridinium electrophiles. The regiochemical outcomes have observable and predictable trends associated with the substituent patterns on the pyridinium electrophile. Often, the substituent effects can be either additive, giving high selectivities, or ablative, giving competing outcomes. Additionally, the nature of the organometallic nucleophilic component was also investigated for its role in the regioselective outcome. The effects of either reactive component are important to both the overall reactivity and site of nucleophilic addition. The utility of these observed trends is demonstrated in a concise, dearomative synthesis of a tricyclic compound shown to have insecticidal activity. This journal is

1H-Indole-Pyridinecarboxamide and 1H-Indole-Piperidinecarboxamide Compounds

Compounds of formula (I): wherein: A represents a divalent radical: wherein: Z represents an oxygen atom or a sulphur atom,R6 represents a hydrogen atom, an alkyl, alkenyl, arylalkyl or polyhaloalkyl group or a substituted, linear or branched alkyl chain, represents a single bond or a double bond,R1, R2, R3 and R4 represent a hydrogen or halogen atom,an alkyl, alkoxy, hydroxy, cyano, nitro, polyhaloalkyl or optionally substituted amino group, or a linear or branched alkyl chain substituted by one or more groups,R5 represents a hydrogen atom or an alkyl, aminoalkyl or hydroxyalkyl group,X and Y represent a hydrogen atom or an alkyl group,Ra, Rb, Rc and Rd represent a hydrogen or halogen atom, an alkyl, hydroxy, alkoxy, cyano, nitro, polyhaloalkyl, optionally substituted amino group, or a substituted, linear or branched alkyl chain,Re represents a hydrogen atom or an alkyl, arylalkyl or alkenyl group or a substituted, linear or branched alkyl chain, their enantiomers, diastereoisomers, and N-oxides, and also addition salts thereof with a pharmaceutically acceptable acid or base.

Substituent effects on formation of cation dimers by weak hydrogen bonds in crystals of carbonyl pyridinium salts of ni(dmit)2

Five 1:1 salts of 3-X-1-methylpyridinium (X = benzoyl, acetyl, methoxycarbonyl, carboxy, and aminocarbonyl; abbreviated as Ben, Ace, Met, Car, and Ami, respectively) cations with a [Ni(dmit)2]- anion ([Ben]+[Ni(dmit)2]- (1), Ace] +[Ni(dmit)2]- (2), [Met]+[Ni(dmit) 2]- (3), [Car]+[Ni(dmit)2] - (4), and [Ami]+[Ni(dmit)2]- (5)) have been synthesized and characterized by single-crystal X-ray analysis and conductivity measurements. In the crystals, three cations 1-3 were found to form dimers by weak C-H...O hydrogen bonds, and the arrangements of cations had a strong relation with the electronic effect of the substituents. The cations of 1-3 formed similar centrosymmetrically associated dimers constructed by weak C-H...O hydrogen bonds, whose geometric parameters had a correlation with the electronic effect of the substituents. A cation of 4 also formed centrosymmetrically associated dimer, but it was made by an O-H...O hydrogen bond as usually observed in the case of carboxylic acid. In contrast with other complex salts, cations of 5 formed one-dimensional structure by C-H...O hydrogen bonding. The conductivities of salts 1, 2, 3, 4, and 5 at room temperature were 1.00 × 10-6, 1.10 × 10-6, 2.86 × 10-6, 9.77 × 10-6, and 8.75 × 10 -7Scm-1, respectively.

NOVEL DRUGS FOR DEMENTIA

The invention is directed to compounds that are prodrugs containing a chemical delivery system (CDS) moiety and a cysteine protease inhibitor moiety. The CDS moiety targets the prodrug to the brain or central nervous system. The cysteine protease inhibitor inhibits cysteine proteases upon release from the prodrug. Cysteine protease inhibitors are effective for treating dementia, Alzheimer's disease and vascular dementia. Targeting the brain or central nervous system offers significant advantages in treating these conditions and diseases. A preferred CDS prodrug is a dihydrotrigoneline CDS moiety coupled to an epoxysuccinyl peptide cysteine protease inhibitor moiety.

Second-order hyperpolarizability of pyridinium cations

The second-order hyperpolarizability (β) of pyridinium cations with cutoff (λco) shorter than 400 nm were studied by semiempirical calculation and the hyper-Rayleigh scattering (HRS) technique. The β value of 4-dimethylaminopyridinium (λco= 390 nm) was evaluated to be about 1.5 times larger than that of p-nitroaniline (λco= 473 nm) in methanolic solution using 1064 nm light as a fundamental beam.

Regioselective synthesis of indolyldihydropyridines. A remarkable solvent effect

The synthesis of 1,2-dihydro-2-(3-indolyl)-1-methylpyridines and 1,4-dihydro-4-(3-indolyl)-1-methylpyridines through the addition of indoles to pyridinium salts in various solvents is described. Selective preparation of 1,2-dihydropyridines is possible performing the reaction in methanol as the solvent, whereas the 1,4-isomers are preferentially formed in dimethyl sulfoxide.

INDUCTION OF CELL ARREST IN G2: STRUCTURAL SPECIFICITY OF TRIGONELLINE

Synthetic analogues of N-methyl nicotinic acid, trigonelline, were prepared to test the structural features necessary for the induction of cellular arrest in G2 in Pisum sativum.Analogues that (1) were regioisomers of trigonelline, (2) possessed different 1,3-substituents, ad (3) contained additional substituents on the pyridine ring were tested for their ability to induce cell arrest in G2 and to anatogize trigonelline induced arrest in G2.Only N-methyl-3-quinoline-carboxic acid and 1-methyl nicotinamide induced cell arrest in G2, and 1-methyl-4-pyridine carboxylic acid and 1-methyl-2-pyridine carboxylic acid were effective trigonelline antagonists.These data further support a specific role for trigonelline in the induction of cell arrest in G2.Key words: Pisum sativum; Leguminosae; pea; trigonelline; structural specificity; structural analogues; cell arrest; G2.