Day: January 6, 2023

Synthesis of N-arylpyridinium salts bearing a nitrone spin trap as potential mitochondria-targeted antioxidants was written by Robertson, Linsey;Hartley, Richard C.. And the article was included in Tetrahedron in 2009.COA of Formula: C11H17N This article mentions the following:

The generation of excess reactive oxygen species (ROS) in mitochondria is responsible for much of the oxidative stress associated with aging, and mitochondrial dysfunction is part of the pathol. of neurodegeneration and type 2 diabetes. Lipophilic pyridinium ions are known to accumulate in mitochondria and this paper describes a general route for the preparation of nitrone-containing N-arylpyridinium salts having a range of lipophilicities, as potential therapeutic antioxidants. The compatibility of nitrones with the Zincke reaction is the key to their synthesis. Their trapping of carbon-centered radicals and the EPR spectra of the resulting nitroxides are reported. In the experiment, the researchers used many compounds, for example, 4-Hexylpyridine (cas: 27876-24-0COA of Formula: C11H17N).

4-Hexylpyridine (cas: 27876-24-0) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. COA of Formula: C11H17N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones was written by Song, Tao;Ma, Zhiming;Ren, Peng;Yuan, Youzhu;Xiao, Jianliang;Yang, Yong. And the article was included in ACS Catalysis in 2020.Reference of 91-02-1 This article mentions the following:

The fabrication of a bifunctional iron nanocomposite catalyst, in which two catalytically active sites of Fe-Nx and Fe phosphate, as oxidation and Lewis acid sites, were simultaneously integrated into a hierarchical N,P-dual doped porous carbon was reported. As a bifunctional catalyst, it exhibited high efficiency for direct oxidative cleavage of alkenes into ketones or their oxidation into 1,2-diketones with a broad substrate scope and high functional group tolerance using TBHP as the oxidant in water under mild reaction conditions. Furthermore, it could be easily recovered for successive recycling without appreciable loss of activity. Mechanistic studies disclose that the direct oxidation of alkenes proceeds via the formation of an epoxide as intermediate followed by either acid-catalyzed Meinwald rearrangement to give ketones with one carbon shorter or nucleophilic ring-opening to generate 1,2-diketones in a cascade manner. This study not only opens up a fancy pathway in the rational design of Fe-N-C catalysts but also offers a simple and efficient method for accessing industrially important ketones and 1,2-diketones from alkenes in a cost-effective and environmentally benign fashion. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Reference of 91-02-1).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Reference of 91-02-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Coordination Assemblies of Co^II/Cu^II/Zn^II/Cd^II with 2,5-Bipyridyl-1,3,4-Oxadiazole and Dicyanamide Anion: Structural Diversification and Properties was written by Du, Miao;Wang, Qian;Li, Cheng-Peng;Zhao, Xiao-Jun;Ribas, Joan. And the article was included in Crystal Growth & Design in 2010.Application In Synthesis of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole This article mentions the following:

This work presents eight coordination assemblies based on divalent metal ions (M = Co^II, Cu^II, Zn^II, and Cd^II), dicyanamide anion (N(CN)₂^–, dca), and two isomeric bent dipyridyl coligands (L), namely, 2,5-bis(3-pyridyl)-1,3,4-oxadiazole (3-bpo) and 2,5-bis(4-pyridyl)-1,3,4-oxadiazole (4-bpo). In the resulting crystalline materials, both bpo and dca tectons generally display the bidentate bridging fashion (except in a mononuclear species), extending the metal centers to afford diverse one-, two-, and three-dimensional (1-D, 2-D, and 3-D) coordination networks that are not commonly observed in M-dca-L systems. Notably, the inclined polycatenated 2-D → 3-D framework and 3-D polyknotting network with the unique 6-connected (4⁴.6¹¹) topol. are formed for the Cu^II and Cd^II species with dca and 4-bpo. For the polymeric Co^II and Cu^II complexes, very weak antiferromagnetic or ferromagnetic interactions are observed between the metal centers due to the μ_1,5-bridging mode of dca, and their magneto-structural correlations have been discussed in detail. The Zn^II and Cd^II complexes show solid-state fluorescent emissions at room temperature In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Application In Synthesis of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Application In Synthesis of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Oximes of 2-acylpyridine and 2-acylquinoline was written by Nakashima, Tatsumi. And the article was included in Yakugaku Zasshi in 1957.Computed Properties of C11H9NO This article mentions the following:

2-NCC₅H₄N reacted with RMgX in Et₂O to give 2-ROCC₅H₄N (I) and the I reacted with NH₂OH.HCl to give the oxime. I prepared were (R. b.p./mm. and m.p. of its oxime given): Me, 65-6°/8, 121°; Et, 80-4°/5, 106°; PhCH₂, 138-42°/2, 157° [picrate, C₁₉H₁₄O₈N₄, m. 161° (decomposition); phenylhydrazone, C₁₉H₁₇N₃, m. 96°]; Ph, 165°/7, 152°. 2-MeC₅H₄N (30 g.) was transformed into 2-PhCH:CHC₅H₄N, then 2-PhCHBrCHBrC₅H₄N, which with alc. KOH yielded 30 g. 2-PhCCC₅H₄N (II), b₅ 174°, m. 78-80°. II with H₂SO₄ kept 48 hrs. at room temperature, the product treated with NH₄OH to pH 8, and extracted with Et₂O gave 2-PhCOCH₂C₅H₄N (III), m. 54°, with poor yield; oxime, m. 120°. Alternatively, treating 2-MeC₅H₄N with Li to form 2-LiCH₂C₅H₄N, and treating this with BzOMe yielded 75% III. Similarly are prepared 2-RCOC₉H₆N (IV) (R, m.p. and m.p. of oxime given): Me, 52-3°, 143.5°; Et, 59-60°, 107°; Ph, 111°, 168-9°. 2-EtO₂CC₉H₆N and PhCH₂CN in EtOH with EtONa yielded 2-PhCH(CN)COC₉H₆N (V), m. 100°. V (1 g.), 1 g. AcOH, 0.7 g. H₂SO₄, and 1.5 ml. H₂O heated at 90-100°, and 1 hr. at 120°, the product poured in ice H₂O, and recrystallized from EtOH gave 0.85 g. 2-PhCH₂COC₉H₆N, m. 78° (oxime, m. 128.5°). 2-PhCCC₉H₆N (19 g.) and 225 ml. H₂SO₄ treated as in III gave 1.5 g. 2-PhCOCH₂C₉H₆N (VI), m. 120-2° (oxime, m. 174-5°). Alternatively, a solution of 1.4 g. Li in 120 ml. Et₂O and 16 g. PhBr treated with 14.5 g. 2-MeC₉H₆N in Et₂O and 7.4 g. BzOMe, the product poured in 60 g. ice and 8 g. NH₄Cl, and the Et₂O removed gave 4.7 g. VI, m. 122°. 2-PhC(:NOH)C₉H₆N in 10 ml. CHCl₃ treated with 0.66 g. SOCl₂, the CHCl₃ and SOCl₂ removed in vacuo, the residue refluxed 3 hrs. with 6N HCl, the product extracted with Et₂O gave 0.5 g. BzOH, m. 119-21°; the HCl layer made alk. and extracted with Et₂O gave 0.4 g. 2-H₂NC₉H₆N, m. 128°. 2-PhC(:NOH)C₆H₄N and 2-acylquinolines do not form complex salt with Fe⁺⁺. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Computed Properties of C11H9NO).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Computed Properties of C11H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Cyclometallated compounds XIV. Kinetic versus thermodynamic control in the reversible cyclopalladation of 2-(2-naphthyloxy)pyridine was written by O’Keefe, Brendan J.;Steel, Peter J.. And the article was included in Inorganic Chemistry Communications in 1999.HPLC of Formula: 4783-68-0 This article mentions the following:

Reaction of 2-(2-naphthyloxy)pyridine with palladium acetate, in acetic acid at room temperature, gives, selectively, the kinetically controlled regioisomer from cyclopalladation in the 1-position, whereas, under reflux, the thermodynamically more stable 3-substituted isomer is exclusively formed. Furthermore, the 1-substituted isomer readily interconverts to the 3-substituted isomer on heating, indicating reversibility of the C-H bond-breaking step. That this is a general phenomenon is demonstrated by deuterium labeling experiments with related ligands. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0HPLC of Formula: 4783-68-0).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.HPLC of Formula: 4783-68-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Syntheses, crystal structures and magnetic study of two binuclear manganese(II) complexes with aromatic N-oxide as bridging ligand was written by Shi, J.-M.;Liu, Z.;Li, W.-N.;Zhao, H. Y.;Liu, L.-D.. And the article was included in Journal of Coordination Chemistry in 2007.Related Products of 3718-65-8 This article mentions the following:

Two new binuclear complexes, [Mn₂(μ-dmpo)₂(SCN)₄(H₂O)₂] (1, dmpo = 3,5-dimethylpyridine N-oxide), [Mn₂(μ-po)₂(H₂O)₆I₂]I₂ (2, po = pyridine N-oxide), were synthesized and their crystal structures determined by x-ray crystallog. Complexes 1 and 2 crystallize in monoclinic, space group P2₁/c, with a 8.8836(18), b 15.450(3), c 15.484(3) Å, β 91.020(3)° for 1, and a 8.8352(13), b 17.927(3), c 8.3338(12) Å, β 103.765(2)° for 2. In each binuclear complex two Mn(II) were bridged by two 3,5-dimethylpyridine N-oxides or by two pyridine N-oxides and the distances between the bridged Mn(II) ions are 3.599 Å for 1 and 3.552 Å for 2. Variable temperature (4-300 K) magnetic measurements were performed for 1 and the susceptibility data were fitted by using a binuclear Mn(II) magnetic coupling formula producing the 2J = -2.17 cm^-1. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Related Products of 3718-65-8).

3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Related Products of 3718-65-8

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Quaternary ammonium surfactant structure determines selective toxicity towards bacteria: mechanisms of action and clinical implications in antibacterial prophylaxis was written by Inacio, Angela S.;Domingues, Neuza S.;Nunes, Alexandra;Martins, Patricia T.;Moreno, Maria J.;Estronca, Luis M.;Fernandes, Rui;Moreno, Antonio J. M.;Borrego, Maria J.;Gomes, Joao P.;Vaz, Winchil L. C.;Vieira, Otilia V.. And the article was included in Journal of Antimicrobial Chemotherapy in 2016.Electric Literature of C17H30BrN This article mentions the following:

Broad-spectrum antimicrobial activity of quaternary ammonium surfactants (QAS) makes them attractive and cheap topical prophylactic options for sexually transmitted infections and perinatal vertically transmitted urogenital infections. Although attributed to their high affinity for biol. membranes, the mechanisms behind QAS microbicidal activity are not fully understood. The authors evaluated how QAS structure affects antimicrobial activity and whether this can be exploited for use in prophylaxis of bacterial infections. Acute toxicity of QAS to in vitro models of human epithelial cells and bacteria were compared to identify selective and potent bactericidal agents. Bacterial cell viability, membrane integrity, cell cycle and metabolism were evaluated to establish the mechanisms involved in selective toxicity of QAS. QAS toxicity normalized relative to surfactant critical micelle concentration showed n-dodecylpyridinium bromide (C12PB) to be the most effective, with a therapeutic index of ∼10 for an MDR strain of Escherichia coli and >20 for Neisseria gonorrhoeae after 1 h of exposure. Three modes of QAS antibacterial action were identified: impairment of bacterial energetics and cell division at low concentrations; membrane permeabilization and electron transport inhibition at intermediate doses; and disruption of bacterial membranes and cell lysis at concentrations close to the critical micelle concentration In contrast, toxicity to mammalian cells occurs at higher concentrations and, as the authors previously reported, results primarily from mitochondrial dysfunction and apoptotic cell death. Thus, short chain (C₁₂) n-alkyl pyridinium bromides have a sufficiently large therapeutic window to be good microbicide candidates. In the experiment, the researchers used many compounds, for example, 1-Dodecylpyridin-1-ium bromide (cas: 104-73-4Electric Literature of C17H30BrN).

1-Dodecylpyridin-1-ium bromide (cas: 104-73-4) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Electric Literature of C17H30BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds was written by Li, Zhibin;Zhang, Yan;Li, Kuiliang;Zhou, Zhenghong;Zha, Zhenggen;Wang, Zhiyong. And the article was included in Science China: Chemistry in 2021.Product Details of 91-02-1 This article mentions the following:

A selective electrochem. oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochem. oxidation The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcs. and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochem. oxidation performance. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Product Details of 91-02-1).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Product Details of 91-02-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electrochemically driven organic monolayer formation on silicon surfaces using alkylammonium and alkylphosphonium reagents was written by Wang, Dong;Buriak, Jillian M.. And the article was included in Surface Science in 2005.Application In Synthesis of 1-Dodecylpyridin-1-ium bromide This article mentions the following:

The functionalization of Si surfaces with organic monolayers, bound through Si-C bonds, is an area of wide interest due to the technol. promise of organosilicon hybrid devices, but also to study fundamental surface reactivity. The use of alkylammonium and alkylphosphonium cations as sources of organic moieties to bind to hydrogen-terminated flat and porous Si is demonstrated. Tetraalkylammonium, tetraalkyl/arylphosphonium reagents, and alkyl pyridinium salts can be used, but trialkylammonium salts cannot as they yield substantial surface oxidation Under electrochem. conditions, either potentiostatic or galvanostatic modes, alkyl groups derived from the NH₄⁺ or phosphonium salts are grafted to the Si surface and are bound through Si-C bonds. Covalent attachment of the organic monolayers to the surface was demonstrated by XPS, AFM scribing, and FTIR. The mechanism may proceed via reduction of the NH₄⁺ salt yielding alkyl radicals, R^•, which may be reduced to R^– and attack surface Si-Si bonds, leading to Si-C bonds, or the formation of silyl anions (≡Si^–) under the cathodic conditions followed by nucleophilic attack on the trialkylammonium cation. In the experiment, the researchers used many compounds, for example, 1-Dodecylpyridin-1-ium bromide (cas: 104-73-4Application In Synthesis of 1-Dodecylpyridin-1-ium bromide).

1-Dodecylpyridin-1-ium bromide (cas: 104-73-4) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Application In Synthesis of 1-Dodecylpyridin-1-ium bromide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Constitution of ricinine was written by Spath, Ernst;Koller, Georg. And the article was included in Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen in 1923.Computed Properties of C7H7NO3 This article mentions the following:

It was shown in the earlier paper that the compounds C₆H₇NO₂ and C₇H₉O₂N obtained from ricinine (I) with concentrated HCl and H₂SO₄, resp., are 1-methyl-4-hydroxy-and 1-methyl-4-methoxy-2-pyridone. It has now been found that when the HO group in ricinic acid (II) is replaced by Cl and the Cl is then replaced by H, the resulting ricinidine (III) is decomposed by alkalies into NH₃ and 1-methyl-2-pyrodone-3-carboxylic acid (IV), which, treated successively with SOCl₂ and NH₃, yields an amide regenerating III on dehydration. These results show that I is 1-methyl-3-cyano-4-methoxy-2-pyridone, CH: CH.C(OMe): C(CN).CO.NMe. The compound C₇H₅ON₂Cl, obtained in 3.5 g. yield from 4 g. II heated 6 hrs. at 100° in a sealed tube with 60 cc. POCl₃, m. 159°, produces sneezing, regenerates II and I when refluxed with Na in MeOH; 1.5 g. in EtOH with 3 g. of 4% Pd-BaSO₄ and 4.5 g. NaOAc hydrogenated under pressure yields 1.256 g. III, b₁₈ 243°, m. 140°, 0.5 g. of which, refluxed 5 hrs. with 2.5 g. Na in 50 cc. MeOH gives 1-methyl-2-pyridone-3-carboxamide (V), m. 216°; 0.095 g. of this on 62 hrs. further refluxing with 2 g. Na in 40 cc. MeOH gives NH₃ and IV, m. 184°. IV is not identical with 2-pyridone-1-acetic acid, m. 220-3°, which was obtained in 0.74 g. yield from 2.3 g. 2-methoxypyridine and 6.97 g. ICH₂CO₂Me heated 12 hrs. on the H₂O bath under a reflux, freed from the excess of methoxypyridine with steam, made strongly alk. and allowed to stand 2 hrs. Nor is IV identical with 1-methyl-2-pyridone-6-carboxylic acid, m. 247-8°, which was obtained in 0.1505 g. yield from the di-Ag salt from 1 g. 2-hydroxypyridine-6-carboxylic acid and 8 cc. MeI heated in a sealed tube 48 hrs. at 100° and 12 hrs. at 130°; on heating, it gives 1-methyl-2-pyridone. IV was synthesized by heating di-Ag 2-hydroxypyridine-3-carboxylate with excess of Mel 40 hrs. at 100°, evaporating off the Mel, extracting the residue with hot alc., evaporating the extract, dissolving the residue in a little H₂O, removing the I with a few drops of aqueous H₂SO₃, making strongly alk. and heating on the H₂O bath 1 hr.; it was also obtained (in better yield -0.992 g.) from 1 g. 2-hydroxypyridine-3-carboxylic acid and 0.48 g. Na in 20 cc. MeOH evaporated to dryness in vacuo, heated 35 hrs. at 100° with 16 cc. MeI, evaporated and heated 1 hr. on the H₂O bath with 2.7 g. KOH in H₂O V was synthesized (yield, 0.425 g.) by heating 0.56 g. IV 1 hr. on the H₂O bath with 5 cc. SOCl₂ and treating the resulting chloride with excess of concentrated aqueous NH₄OH; distilled in vacuo with P₂O₅ it gives III, while 0.037 g. heated 5 hrs. at 100° in a sealed tube with 1 cc. POCl₃ yields 2-chloro-3-cyanopyridine (VI) and 0.014 g. III. 2-Chloropyridine-3-carboxamide (0.736 g. from 1 g. of the acid refluxed 4 hrs. with 2 g. PCl₆ and 25 cc. POCl₃ and then 4 hrs. longer with 2 g. more of PCl₅, freed from the P chlorides in vacuo and allowed to stand some time with concentrated NH₄OH), m. 163-4°; 0.05 g. cautiously heated in vacuo with 0.078 g. P₂O₅ yields VI, m. 103-5°, also obtained by heating 0.04 g. III at 150° in a sealed tube with 0.045 g. POCl₃ and 0.42 g. PCl₅ or by heating 0.318 g. of the amide 16 hrs. at 100° in a bomb with 15 cc. POCl₃. The formation of VI from III confirms the view that III is 1-methyl-3-cyano-2-pyridone. In the experiment, the researchers used many compounds, for example, 1-Methyl-6-oxo-1,6-dihydropyridine-2-carboxylic acid (cas: 59864-31-2Computed Properties of C7H7NO3).

1-Methyl-6-oxo-1,6-dihydropyridine-2-carboxylic acid (cas: 59864-31-2) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Computed Properties of C7H7NO3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem