Category: pyridine-derivatives

Mechanism of decarboxylation of 1,3-dimethylorotic acid. A model for orotidine 5′-phosphate decarboxylase was written by Beak, Peter;Siegel, Brock. And the article was included in Journal of the American Chemical Society in 1976.Reference of 59864-31-2 This article mentions the following:

The decarboxylation of 1,3-dimethylorotic acid (I) is shown to proceed by sep. pH-determined pathways in sulfolane at 180-220°. Although a process involving ionization of I is the major pathway in the presence of excess base, decarboxylation is initiated by zwitterion formation in the neutral solvent. Measurements of the rate of loss of CO2 from 6-carboxy-2,4-dimethoxypyrimidine and 1-methyl-2,4-dimethoxypyrimidinium-6-carboxylate betaine (II) are used to estimate the equilibrium and rate constants for the zwitterionic pathway. Comparison of the rate constant for decarboxylation of II with kcat for orotidine 5′-phosphate decarboxylase shows that the biol. catalysis can be satisfactorily accounted for if the enzyme provides a site which displaces the equilibrium in favor of the zwitterionic form of orotidylic acid. It is also noted that the inhibitor, 6-azauridine monophosphate, which has a greater affinity for the enzyme than does the substrate, provides a partial model for the intermediate formed on loss of CO2 from the zwitterion. In the experiment, the researchers used many compounds, for example, 1-Methyl-6-oxo-1,6-dihydropyridine-2-carboxylic acid (cas: 59864-31-2Reference of 59864-31-2).

1-Methyl-6-oxo-1,6-dihydropyridine-2-carboxylic acid (cas: 59864-31-2) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Reference of 59864-31-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

4-Hydroxy Pyridinium Triflate@SiO₂ Nanoparticles as a Novel Efficient Catalyst for Fries Rearrangement of Aryl Esters with High Selectivity was written by Ghalehbandi, Shermineh Sadat;Ghazanfari, Dadkhoda;Ahmadi, Sayed Ali;Sheikhhosseini, Enayatollah. And the article was included in Current Organic Synthesis in 2020.SDS of cas: 626-64-2 This article mentions the following:

A simple, fast and new method for the Fries rearrangement of aryl esters was developed. 4-Hydroxy pyridinium triflate functionalized silica was a very efficient, reusable and economically available catalyst for the Fries rearrangement in solvent-free condition and under microwave irradiation Also, a notable selectivity was observed in the presence of 4-hydroxy pyridinium triflate functionalized silica. Selectivity, shorter reaction time, high yield and easy work-up are advantages of this synthetic method. In the experiment, the researchers used many compounds, for example, Pyridin-4-ol (cas: 626-64-2SDS of cas: 626-64-2).

Pyridin-4-ol (cas: 626-64-2) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. 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. SDS of cas: 626-64-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Co-crystallization of oxadiazole-bridged pyridyl-N-oxide building modules with R-aromatics (R = -OH, -NH₂ and -COOH) was written by Hou, Gui-Ge;Ma, Jian-Ping;Wang, Le;Wang, Ping;Dong, Yu-Bin;Huang, Ru-Qi. And the article was included in CrystEngComm in 2010.Application of 15420-02-7 This article mentions the following:

The reaction of oxadiazole bridging pyridyl-N-oxides (2,5-bis(4-pyridyl-N-oxide)-1,3,4-oxadiazole (A1) and 2-(4-pyridyl)-5-(4-pyridyl-N-oxide)-1,3,4-oxadiazole (A2)) with different substituted aromatics (R-aromatics, R = -OH, -NH₂, -COOH) were studied. Eight new organic co-crystals of 1-8 were synthesized and characterized by elemental anal., FTIR spectroscopy, ¹H NMR and single-crystal x-ray diffraction. The results display the distinct substituent effect on the hydrogen-bonded self-assembly systems. The luminescent properties of A1-A2 and 1-8 were studied in the solid state. In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Application of 15420-02-7).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) 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. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Application of 15420-02-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Bodipy-C₆₀ triple hydrogen bonding assemblies as heavy atom-free triplet photosensitizers: preparation and study of the singlet/triplet energy transfer was written by Guo, Song;Xu, Liang;Xu, Kejing;Zhao, Jianzhang;Kucukoz, Betul;Karatay, Ahmet;Yaglioglu, Halime Gul;Hayvali, Mustafa;Elmali, Ayhan. And the article was included in Chemical Science in 2015.Application of 1075-62-3 This article mentions the following:

Supramol. triplet photosensitizers based on hydrogen bonding-mediated mol. assemblies were prepared Three thymine-containing visible light-harvesting Bodipy derivatives (B-1, B-2 and B-3, which show absorption at 505 nm, 630 nm and 593 nm, resp.) were used as H-bonding modules, and 1,6-diaminopyridine-appended C₆₀ was used as the complementary hydrogen bonding module (C-1), in which the C₆₀ part acts as a spin converter for triplet formation. Visible light-harvesting antennae with methylated thymine were prepared as references (B-1-Me, B-2-Me and B-3-Me), which are unable to form strong H-bonds with C-1. Triple H-bonds are formed between each Bodipy antenna (B-1, B-2 and B-3) and the C₆₀ module (C-1). Singlet energy transfer from the Bodipy antenna to the C₆₀ module was confirmed by fluorescence quenching studies. The intersystem crossing of the latter produced the triplet excited state. The nanosecond transient absorption spectroscopy showed that the triplet state is either localized on the C₆₀ module (for assembly B-1·C-1), or on the styryl-Bodipy antenna (for assemblies B-2·C-1 and B-3·C-1). Intra-assembly forward-backward (ping-pong) singlet/triplet energy transfer was proposed. In contrast to the H-bonding assemblies, slow triplet energy transfer was observed for the non-hydrogen bonding mixtures As a proof of concept, these supramol. assemblies were used as triplet photosensitizers for triplet-triplet annihilation upconversion. In the experiment, the researchers used many compounds, for example, N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3Application of 1075-62-3).

N-(6-Aminopyridin-2-yl)acetamide (cas: 1075-62-3) 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. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Application of 1075-62-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Potassium Amide-Catalyzed Benzylic C-H Bond Addition of Alkylpyridines to Styrenes was written by Zhai, Dan-Dan;Zhang, Xiang-Yu;Liu, Yu-Feng;Zheng, Lei;Guan, Bing-Tao. And the article was included in Angewandte Chemie, International Edition in 2018.Formula: C8H11N This article mentions the following:

The benzylic functionalization of alkylpyridines is an important pathway for pyridine derivatives synthesis. The reaction partners, however, were mostly limited to highly reactive polar electrophiles. Herein, we report a potassium amide-catalyzed selective benzylic C-H bond addition of alkylpyridines to styrenes. Potassium bis(trimethylsilyl)amide (KHMDS), a readily available Bronsted base, showed excellent catalytic activity and chemoselectivity. A series of alkylpyridine derivatives, including benzylic quaternary carbon substituted pyridines, were obtained in good to high yield. Preliminary mechanistic studies revealed that the deprotonation equilibrium is probably responsible for the excellent selectivity. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Formula: C8H11N).

2-Isopropylpyridine (cas: 644-98-4) 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.Formula: C8H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A simultaneous oxidation of isomeric benzyl- and isopropylpyridines was written by Opeida, I. A.;Matvienko, A. G.;Efimova, I. V.;Zalevskaya, N. M.. And the article was included in Ukrainskii Khimicheskii Zhurnal (Russian Edition) in 1986.SDS of cas: 644-98-4 This article mentions the following:

A kinetic study was reported of the oxidation of the following binary mixture: (1) 3-isopropylpyridine with 2-, 3-, and 4-benzylpyridine and Ph₂CH₂; (2) 2-benzylpyridine with 2-, 3-, and 4-isopropylpyridine and cumene; and (3) 3-isopropylpyridine with 4-benzylpyridine. The reactivity of the isopropyl- and benzylpyridine increased in the order 4 < 2 < 3. Ph₂CH₂ was more reactive than the benzylpyridines, and cumene was more reactive than the isopropylpyridines. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4SDS of cas: 644-98-4).

2-Isopropylpyridine (cas: 644-98-4) 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. SDS of cas: 644-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides was written by Cristau, Henri-Jean;Cellier, Pascal P.;Spindler, Jean-Francis;Taillefer, Marc. And the article was included in Chemistry – A European Journal in 2004.Safety of 2-Phenoxypyridine This article mentions the following:

Mild, efficient, copper-catalyzed N-arylation procedures for nitrogen heterocycles, amides, carbamates, and C-arylation procedures for malonic acid derivatives have been developed that afford high yields of arylated products, e.g., I, with excellent selectivity. The N-arylation of imidazole with aryl bromides or iodides was found to be greatly accelerated by inexpensive, air-stable catalyst systems, combining catalytic copper salts or oxides with a set of structurally simple chelating ligands. The reaction was shown to be compatible with a broad range of aryl halides, encompassing sterically hindered, electron-poor, and electron-rich ones, providing the arylated products under particularly mild conditions. The lower limit in ligand and catalyst loading and the scope of Ullmann-type condensations catalyzed by complexes bearing those ligands with respect to the nucleophile class have also been investigated. Chelating Schiff base Chxn-Py-Al generated a remarkably general copper catalyst for N-arylation of pyrrole, indole, 1,2,4-triazole, amides, and carbamates; and C-arylation of di-Et malonate, Et cyanoacetate, and malononitrile with aryl iodides under mild conditions. The method reported here was successful with regard to Ullmann-type arylation. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Safety of 2-Phenoxypyridine).

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. 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. Safety of 2-Phenoxypyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Surface properties of the binary mixed systems of alkylpyridinium halides and sodium alkylsulfonates was written by Goralczyk, Danuta;Hac, Katarzyna;Wydro, Pawel. And the article was included in Colloids and Surfaces, A: Physicochemical and Engineering Aspects in 2003.Synthetic Route of C17H30BrN This article mentions the following:

Surface properties of the binary mixed systems of decyl- and dodecylpyridinium chloride or bromide and Na pentyl- and heptylsulfonate were studied. The surface tension of solutions of equimolar mixtures of surfactants and individual surfactants was measured, and the composition of mixed monolayers and surface interaction parameter β were calculated with the regular solution theory. Results indicate that the properties of mixed films depend on both ionic strength and the kind of added inorganic electrolyte. With the increase of inorganic electrolyte concentration, the content of more surface active ions in the adsorption films enhances and is the highest in the presence of NaI and the smallest when solutions contain NaCl. Mutual interactions in mixed adsorbed films are attractive. However, the strength of interaction weakens with the increase of ionic strength and depends on the kind of inorganic ions in the order: Cl^–>Br^–>I^–. In the experiment, the researchers used many compounds, for example, 1-Dodecylpyridin-1-ium bromide (cas: 104-73-4Synthetic Route of C17H30BrN).

1-Dodecylpyridin-1-ium bromide (cas: 104-73-4) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Synthetic Route of C17H30BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A new chelation-assistance mode for a ruthenium-catalyzed silylation at the C-H bond in aromatic ring with hydrosilanes was written by Kakiuchi, Fumitoshi;Igi, Kimitaka;Matsumoto, Mitsutaka;Hayamizu, Tomoo;Chatani, Naoto;Murai, Shinji. And the article was included in Chemistry Letters in 2002.Related Products of 4783-68-0 This article mentions the following:

Ru-catalyzed reactions of aromatic compounds having an amino group or a heteroaromatic ring as a directing group with triethylsilane gave the corresponding ortho silylated products in good to excellent yields. E.g., 2-benzylpyridine reacts with HSiEt₃ in the presence of 6 mol% Ru₃(CO)₁₂ and norbornene/toluene to give 2-[2-(Et₃Si)C₆H₄]C₅H₄N (77% yield) or 2-[2,6-(Et₃Si)₂C₆H₃]C₅H₄N (13% yield). In contrast previous results, in which the reactive substrates with π-conjugation between the hetero atom in the directing group and the C atom possessing the C-H bond to be cleaved were used, the present reaction proceeds in cases of substrates having no such π-conjugation. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Related Products of 4783-68-0).

2-Phenoxypyridine (cas: 4783-68-0) 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. 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.Related Products of 4783-68-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Chemistry of 3-hydroxypyridine. Part 1. Bromination and iodination of 3-hydroxypyridine was written by Koch, Volker;Schnatterer, Stefan. And the article was included in Synthesis in 1990.Synthetic Route of C5H3Br2NO This article mentions the following:

Bromination of 3-hydroxypyridine (I) with Br₂ in aqueous NaOH gave 2-bromo, 2,6-dibromo, and 2,4-dibromo derivatives Iodination of I in aqueous Na₂CO₃ gave 2-iodo, 2,6-diiodo, and 2,4,6-triiodo derivatives Similarly, iodination of 2-bromo-3-hydroxypyridine gave 2-bromo-6-iodo- and 2-bromo-4,6-diiodo-3-hydroxypyridine. In the experiment, the researchers used many compounds, for example, 2,6-Dibromo-3-hydroxypyridine (cas: 6602-33-1Synthetic Route of C5H3Br2NO).

2,6-Dibromo-3-hydroxypyridine (cas: 6602-33-1) 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. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Synthetic Route of C5H3Br2NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem