Tag: 100-200

Alkylation of pyridine 1-oxides and related compounds with activated acetylenes. A novel molecular rearrangement of heteroaromatic N-oxides was written by Abramovitch, Rudolph A.;Grins, George;Rogers, Richard B.;Shinkai, Ichiro. And the article was included in Journal of the American Chemical Society in 1976.Computed Properties of C7H9NO This article mentions the following:

The reaction of pyridine 1-oxide with phenylcyanoacetylene gives the 3-alkylated derivative (I) as the main product together with minor amounts of II, III and IV. With substituted pyridine 1-oxides and with quinoline 1-oxide the products of 3-alkylation are also formed unless the 3 and 5 positions are blocked. The 3-alkylated products arise from the initial 1,2-dihydro adduct by a [σ2s + π2a + π4s] rearrangement, followed by regiosp. cyclopropane ring opening to the 3-alkylated derivatives In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Computed Properties of C7H9NO).

3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) 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.Computed Properties of C7H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Design, Synthesis, and Biological Evaluation of Novel Matrix Metalloproteinase Inhibitors As Potent Antihemorrhagic Agents: From Hit Identification to an Optimized Lead was written by Orbe, Josune;Sanchez-Arias, Juan A.;Rabal, Obdulia;Rodriguez, Jose A.;Salicio, Agustina;Ugarte, Ana;Belzunce, Miriam;Xu, Musheng;Wu, Wei;Tan, Haizhong;Ma, Hongyu;Paramo, Jose A.;Oyarzabal, Julen. And the article was included in Journal of Medicinal Chemistry in 2015.Reference of 51834-97-0 This article mentions the following:

Growing evidence suggests that matrix metalloproteinases (MMP) are involved in thrombus dissolution; then, considering that new therapeutic strategies are required for controlling hemorrhage, we hypothesized that MMP inhibition may reduce bleeding by delaying fibrinolysis. Thus, we designed and synthesized a novel series of MMP inhibitors to identify potential candidates for acute treatment of bleeding. Structure-based and knowledge-based strategies were utilized to design this novel chem. series, α-spiropiperidine hydroxamates, of potent and soluble (>75 μg/mL) pan-MMP inhibitors. The initial hit was progressed to an optimal lead I. Racemic I showed a remarkable in vitro phenotypic response and outstanding in vivo efficacy; in fact, the mouse bleeding time at 1 mg/kg was 0.85 min compared to 29.28 min using saline. In addition, I displayed an optimal ADME and safety profile (e.g., no thrombus formation). Its corresponding enantiomers were separated, leading to the preclin. candidate (R)-I. In the experiment, the researchers used many compounds, for example, 5-Hydroxy-2-methoxylpyridine (cas: 51834-97-0Reference of 51834-97-0).

5-Hydroxy-2-methoxylpyridine (cas: 51834-97-0) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Reference of 51834-97-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

N-Oxides of the methylpyridines. III. Action of acetic an-hydride on the N-oxides of 3-picoline and 3,5-lutidine was written by Rooyen, G. F. van;Brink, C. V. D. M.;Villiers, P. A. de. And the article was included in Tydskrif vir Natuurwetenskappe in 1964.Application of 3718-65-8 This article mentions the following:

3-Picoline (I) N-oxide [Ochiai, CA 48, 3359i), except that the reaction was catalyzed by concentrated H₂SO₄] (70.1 g.) and 108 g. Ac₂O refluxed 4 hrs. at 140-50°, the mixture concentrated in vacuo, treated with 20 ml. H₂O, and again concentrated in vacuo, the residue made alk. with concentrated aqueous Na₂CO₃ and extracted with CHCl₃, the extract dried and concentratedin vacuo [the residue (A) was saved], and the distillate refractionated gave an oil which treated with excess saturated aqueous picric acid gave 0-2% I picrate, m. 145-7°, and 11% 3 other picrates of unidentified bases, m. 184-6°, 204-5.5°, and 281-2°; the picrate m. 1846° was converted to the free base, m. 145-7° (C₆H₆). Residue A dissolved in H₂O, made strongly alk. with concentrated aqueous NaOH, and extracted with CHCl₃ [the aqueous soluble solution (A) was saved], the extract evaporated, the residue extracted with cyclohexane, and the extract purified by chromatography on Al₂O₃ gave 5-10% 3-methyl-N-(5-methyl-2-pyridyl)-2-pyridone (II), m. 107.5-8.5° (cyclohexane); the residue remaining after extraction with cyclohexane chromatographed on Al₂O₃ with 3:2 CCl₄-C₆H₆ and eluted with CCl₄-C₆H₆ and then CHCl₃ gave an oil, whose picrate m. 137.5-8.5°, after rechromatography of the oil, and whose HgCl₂ complex m. 151-3° (the oil may possibly be 5,5′-dimethyl-2,2′-bipyridyl); further elution with EtOH gave 0.5% 2-amino-5-methylpyridine (IIa) (picrate m. 247.5-9.5°; HgCl₂ complex m. 159-60°). Solution A acidified with HCl, made slightly alk. with aqueous NH₃ (Congo paper), extracted with CHCl3, evaporated in vacuo, the residue extracted with CHCl₃, and the combined CHCl₃ extracts concentrated gave 10.03 g. crude 5-methyl-2-pyridone (III), which recrystallized from 1:1 C₆H₆-hexane gave III, m. 185-6° (C₆H₆-hexane) (picrate m. 1467.5°; HgCl₂ complex m. 206.5-8.5°); the mother liquor chromatographed on activated Al₂O₃ and the column eluted with C₆H₆ gave a mixture (IIIa) of III and 3-methyl-2-pyridone (IV); further elution with CHCl₃ gave addnl. III, and 10% AcOH elulion gave some IV and a small amount unidentified compound, m. 226.5-31.0°. Repeated chromatography of IIIa gave 3.46 g. IV, m. 140-1.5° (C₆H₆); picrate m. 157.5-9.0°; HgCl₂ complex m. 131.5-2.0°. 3,5-Lutidine (V) N-oxide (VI) (Kambara, et al., CA 46, 1795f) (37.9 g.) refluxed 2.25 hrs. at 160° with 36 g. Ac₂O, 10 ml. Ac₂O added, and the mixture heated 2.75 hrs. while gradually allowing the temperature to drop to 146° and worked up gave a CHCl₃ distillate containing no products and 32 g. oily alkali-insoluble fraction (A) and a 7.85 g. semi-crystalline alk.-soluble fraction (B). Fraction A chromatographed on activated Al₂O₃ and eluted with CCl₄ gave 23.7 g. oil, which extracted with petr. ether gave 7.32 g. petr. ethersol. I (picrate m. 244-5°) and 7% petr. ether-insoluble 3,5-dimethyl-N-(3,5-dimethyl-2-pyridyl)-2-pyridone, m. 104-5° (1:1 C₆H₆ hexane); further elution with C₆H₆ gave 2.7 g. unchanged VI (picrate m. 135-6.5°). Fraction B chromatographed on Al₂O₃ and eluted with CHCl₃ gave 4% 3,5-dimethyl-2-pyridone, m. 118.5-19.5° (hexane); picrate m. 208.5-10.0°. 5-Methyl-2bromopyridine [m. 152.5° (3:1 C₆H₆-CHCl₃); picrate m. 1267.5°] (0.85 g.), 0.65 g. IV Na derivative, and 25 mg.Cu powder refluxed 5 hrs. and worked up (CA 51, 5067h) gave 300 mg. II, m. 107.5-8.5° (cyclohexane). II (300 mg.), 1.5 g. NaOH, and 1 ml. H₂O refluxed 20 min. at 145-50° and the mixture cooled, diluted with 10 ml. H₂O, acidified with dilute HCl, made just alk. with aqueous NH₃, and extracted with CHCl₃ gave (from the extract) oily IIa; picrate m. 247.5-9.5°. Ir and uv data were given. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Application of 3718-65-8).

3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) 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 groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Application of 3718-65-8

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Regioselective Amidomethylation of 4-Chloro-3-fluoropyridine by Metalation and Minisci-Type Reactions was written by Papaioannou, Nikolaos;Fray, M. Jonathan;Rennhack, Andreas;Sanderson, Thomas J.;Stokes, Jamie E.. And the article was included in Journal of Organic Chemistry in 2020.COA of Formula: C6H6FN This article mentions the following:

The synthesis of a series of 2-amidomethylated pyridines (3-8) was investigated, starting from 4-chloro-3-fluoropyridine. Kinetic deprotonation at -75°C followed by reaction with DMF gave 2-formyl-4-chloro-3-fluoropyridine 10 regioselectively, which was converted to 2-aminomethyl analog 1 via sulfinamide 2. Alternatively, Minisci-type amidomethylation under Ag⁺/persulfate or photoredox-mediated conditions using a series of amino acid derivatives gave (3-8, 19, and 34) in 30-74% yield and isomer ratios in the range 6.7:1 to > 50:1. The latter methods gave overall yields similar to that of the deprotonation approach, but were shorter and more amenable to scale-up. In particular, N-Boc analog 8 was obtained in a single step. The amidomethylations of another six 3-fluoropyridines under the photoredox conditions were briefly examined In the experiment, the researchers used many compounds, for example, 3-Fluoro-4-methylpyridine (cas: 399-88-2COA of Formula: C6H6FN).

3-Fluoro-4-methylpyridine (cas: 399-88-2) 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.COA of Formula: C6H6FN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis, CYP 450 evaluation, and docking simulation of novel 4-aminopyridine and coumarin derivatives was written by Ghalehshahi, Hajar G.;Balalaie, Saeed;Sohbati, Hamid R.;Azizian, Homa;Alavijeh, Mohammad S.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2019.Computed Properties of C7H7ClN2 This article mentions the following:

Four series of novel compounds based on 4-aminopyridine, glatiramer acetate, pyrone, and coumarin backbones were sufficiently synthesized and identified by spectroscopic methods. CYP enzyme inhibition assays of five predominate human P 450 isoenzymes indicate that all compounds, except for 4-hydrazide pyridine 1c, seem to be less toxic than 4-aminopyridine. Further investigation of the compounds using mol. docking experiments revealed different, the same, or stronger binding modes for most of the synthesized compounds, with both polar and hydrophobic interactions with the 1WDA and 1J95 receptors compared to benzoyl L-arginine amide and 4-aminopyridine, resp. These results introduce the synthesized compounds as K⁺ channel blockers that could be considered for in vivo CNS disease studies. In the experiment, the researchers used many compounds, for example, 1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3Computed Properties of C7H7ClN2).

1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3) 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. 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. Computed Properties of C7H7ClN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles was written by Reidl, Tyler W.;Bandar, Jeffrey S.. And the article was included in Journal of the American Chemical Society in 2021.Safety of 4-Methylpicolinonitrile This article mentions the following:

Lewis basic salts promoted organotrimethylsilane coupling with (hetero)aryl nitriles, sulfones and chlorides as a new route to 1,1-diarylalkanes. This method combined the substrate modularity and selectivity characteristic of cross-coupling with the practicality of a base-promoted protocol. In addition, a Lewis base strategy enabled a complementary scope to existing methods, employed stable and easily prepared organosilanes and achieved selective arylation in the presence of acidic functional groups. The utility of this method was demonstrated by the synthesis of pharmaceutical analogs and its use in multicomponent reactions. In the experiment, the researchers used many compounds, for example, 4-Methylpicolinonitrile (cas: 1620-76-4Safety of 4-Methylpicolinonitrile).

4-Methylpicolinonitrile (cas: 1620-76-4) 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. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Safety of 4-Methylpicolinonitrile

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

An Ullmann C-O Coupling Reaction Catalyzed by Magnetic Copper Ferrite Nanoparticles was written by Yang, Shuliang;Wu, Cunqi;Zhou, Hua;Yang, Yanqin;Zhao, Yongxia;Wang, Chenxu;Yang, Wei;Xu, Jingwei. And the article was included in Advanced Synthesis & Catalysis in 2013.COA of Formula: C11H9NO This article mentions the following:

Herein, an efficient method for the Ullmann C-O coupling reaction between various kinds of phenols and aryl halides, including amino, ketone, cyano, Me, methoxy, fluoro, chloro and bromo derivatives, is described. The catalyst used, copper ferrite (CuFe₂O₄) nanoparticles, are easily made, air-stable, and of low cost. The catalyst can be recycled easily just by using an external magnet. Even in the presence of sensitive substituents, the reaction proceeds successfully to provide the desired products in high yields without protection of other functional groups. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0COA of Formula: C11H9NO).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. 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.COA of Formula: C11H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Chemoinformatics Profiling of Ionic Liquids-Uncovering Structure-Cytotoxicity Relationships With Network-like Similarity Graphs was written by Cruz-Monteagudo, Maykel;Cordeiro, Maria Natalia Dias Soeiro. And the article was included in Toxicological Sciences in 2014.Synthetic Route of C10H16ClN This article mentions the following:

Ionic liquids (ILs) constitute one of the hottest areas in chem. since they have become increasingly popular as reaction and extraction media. Their almost limitless structural possibilities, as opposed to limited structural variations within mol. solvents, make ILs “designer solvents.”. They also have been widely promoted as “green solvents” although their claimed relative nontoxicity has been frequently questioned. The Thinking in Structure-Activity Relationships (T-SAR) approach has proved to be an efficient method to gather relevant toxicol. information of analog series of ILs. However, when data sets significantly grow in size and structural diversity, the use of computational models becomes essential. The authors provided such a computational solution in a previous work by introducing a reliable, predictive, simple, and chem. interpretable Classification and Regression Tree (CART) classifier enabling the prioritization of ILs with a favorable cytotoxicity profile. Even so, an efficient and exhaustive mining of SAR information goes beyond analog compound series and the applicability domain of quant. SAR modeling. So, the authors decided to complement the authors’ previous findings based on the use of the CART classifier by applying the network-like similarity graph (NSG) approach to the mining of relevant structure-cytotoxicity relationship (SCR) trends. Finally, the SCR information concurrently gathered by both, quant. (CART classifier) and qual. (NSG) approaches was used to design a focused combinatorial library enriched with potentially safe ILs. In the experiment, the researchers used many compounds, for example, 1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3Synthetic Route of C10H16ClN).

1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3) 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. 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.Synthetic Route of C10H16ClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Amidinyl Radical Formation through Anodic N-H Bond Cleavage and Its Application in Aromatic C-H Bond Functionalization was written by Zhao, Huai-Bo;Hou, Zhong-Wei;Liu, Zhan-Jiang;Zhou, Ze-Feng;Song, Jinshuai;Xu, Hai-Chao. And the article was included in Angewandte Chemie, International Edition in 2017.Category: pyridine-derivatives This article mentions the following:

We report herein an atom-economical and sustainable approach to access amidinyl radical intermediates through the anodic cleavage of N-H bonds. The resulting nitrogen-centered radicals undergo cyclizations with (hetero)arenes, followed by rearomatization, to afford functionalized tetracyclic benzimidazoles, e.g., I (X-rays crystal structure shown), in a highly straightforward and efficient manner. This metal- and reagent-free C-H/N-H cross-coupling reaction exhibits a broad substrate scope and proceeds with high chemoselectivity. In the experiment, the researchers used many compounds, for example, 2-(Methylamino)nicotinonitrile (cas: 52583-87-6Category: pyridine-derivatives).

2-(Methylamino)nicotinonitrile (cas: 52583-87-6) 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. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis and properties of [(thiocarbamoyl)methyl]pyridinium (isoquinolinium) ylides was written by Berseneva, V. S.;Bakulev, V. A.;Mokrushin, V. S.;Lebedev, A. T.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1989.Synthetic Route of C7H7ClN2 This article mentions the following:

Treating pyridinium or isoquinolinium ylides I (R = CN) with H₂S in EtOH containing NaOEt gave ylides I (R = CSNH₂). The isoquinoline derivatives were cyclized by 1-chloro-2,4-dinitrobenzene to give 32% imidazoloisoquinoline II. Addnl. obtained from I were 15 and 30% imidazolopyridine and isoquinolines III, resp. In the experiment, the researchers used many compounds, for example, 1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3Synthetic Route of C7H7ClN2).

1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3) 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. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Synthetic Route of C7H7ClN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem