Pyridine-derivatives

Formula: C6H5NO2In 2021 ,《Mechanistic investigation of the aerobic oxidation of 2-pyridylacetate coordinated to a Ru(II) polypyridyl complex》 was published in Dalton Transactions. The article was written by Sousa, Sinval F.; Ertem, Mehmed Z.; Faustino, Leandro A.; Machado, Antonio Eduardo. H.; Concepcion, Javier J.; Maia, Pedro I. S.; Patrocinio, Antonio Otavio T.. The article contains the following contents:

A new ruthenium polypyridyl complex, [Ru(bpy)2(acpy)]+ (acpy = 2-pyridylacetate, bpy = 2,2′-bipyridine), was synthesized and fully characterized. Distinct from the previously reported analog, [Ru(bpy)2(pic)]+ (pic = 2-pyridylcarboxylate), the new complex is unstable under aerobic conditions and undergoes oxidation to yield the corresponding α-keto-2-pyridyl-acetate (acpyoxi) coordinated to the RuII center. The reaction is one of the few examples of C-H activation at mild conditions using O2 as the primary oxidant and can provide mechanistic insights with important implications for catalysis. Theor. and exptl. investigations of this aerobic oxidative transformation indicate that it takes place in two steps, first producing the α-hydroxo-2-pyridyl-acetate analog and then the final product. The observed rate constant for the first oxidation was in the order of 10-2 h-1. The reaction is hindered in the presence of coordinating solvents indicating the role of the metal center in the process. Theor. calculations at the M06-L level of theory were performed for multiple reaction pathways in order to gain insights into the most probable mechanism. Authors results indicate that O2 binding to [Ru(bpy)2(acpy)]+ is favored by the relative instability of the six-ring chelate formed by the acpy ligand and the resulting RuIII-OO ̇- superoxo is stabilized by the carboxylate group in the coordination sphere. C-H activation by this species involves high activation free energies (ΔG‡ = 41.1 kcal mol-1), thus the formation of a diruthenium μ-peroxo intermediate, [(RuIII(bpy)2(O-acpy))2O2]2+ via interaction of a second [Ru(bpy)2(acpy)]+ was examined as an alternative pathway. The dimer yields two RuIV:O centers with a low ΔG‡ of 2.3 kcal mol-1. The resulting RuIV:O species can activate C-H bonds in acpy (ΔG‡ = 23.1 kcal mol-1) to produce the coordinated α-hydroxo-2-pyridylacetate. Further oxidation of this intermediate leads to the α-keto-2-pyridyl-acetate product. The findings provide new insights into the mechanism of C-H activation catalyzed by transition-metal complexes using O2 as the sole oxygen source. In the experimental materials used by the author, we found Picolinic acid(cas: 98-98-6Formula: C6H5NO2)

Picolinic acid(cas: 98-98-6) is used as a chelate for alkaline earth metals. Used to prepare picolinato ligated transition metal complexes. In synthetic organic chemistry, has been used as a substrate in the Mitsunobu reaction and in the Hammick reaction.Formula: C6H5NO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of C5H3Br2NIn 2020 ,《Controlling Singlet Fission with Coordination Chemistry-Induced Assembly of Dipyridyl Pyrrole Bipentacenes》 was published in ACS Central Science. The article was written by Ribson, Ryan D.; Choi, Gyeongshin; Hadt, Ryan G.; Agapie, Theodor. The article contains the following contents:

Singlet fission has the potential to surpass current efficiency limits in next-generation photovoltaics and to find use in quantum information science. Despite the demonstration of singlet fission in various materials, there is still a great need for fundamental design principles that allow for tuning of photophys. parameters, including the rate of fission and triplet lifetimes. Here, we describe the synthesis and photophys. characterization of a novel bipentacene dipyridyl pyrrole (HDPP-Pent) and its Li- and K-coordinated derivatives HDPP-Pent undergoes singlet fission at roughly 50% efficiency (τSF = 730 ps), whereas coordination in the Li complex induces significant structural changes to generate a dimer, resulting in a 7-fold rate increase (τSF = 100 ps) and more efficient singlet fission with virtually no sacrifice in triplet lifetime. We thus illustrate novel design principles to produce favorable singlet fission properties, wherein through-space control can be achieved via coordination chem.-induced multipentacene assembly. Series of ligand-bridged bipentacenes display differential rates/yields of singlet fission as a result of distinct solution-state structures arising from the identity of the coordinated alkali metal. In the experimental materials used by the author, we found 2,6-Dibromopyridine(cas: 626-05-1Electric Literature of C5H3Br2N)

2,6-Dibromopyridine(cas: 626-05-1) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Electric Literature of C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Product Details of 626-05-1In 2021 ,《Rare Fluorescence Red-Shifted Metal-Organic Framework Sensor for Methylamine Derived from an N-Donor Ligand》 was published in Crystal Growth & Design. The article was written by Yao, Shu-Li; Xu, Hui; Zheng, Teng-Fei; Liu, Sui-Jun; Chen, Jing-Lin; Wen, He-Rui. The article contains the following contents:

A three-dimensional (3D) metal-organic framework (MOF) [Cd(bbip)(NDC)]n(JXUST-8, bbip = 2,6-bis(benzimidazol-1-yl)pyridine, and H2NDC = 2,6-naphthalenedicarboxylic acid) with 8-connected bcg topol. was solvothermally synthesized and fully characterized. The fluorescence experiments demonstrate that JXUST-8 could selectively distinguish methylamine (MA) by fluorescence red shift, and the detection limit is 0.341 ppm. It is noteworthy that red shift emission could enlarge the fluorescence signal, which is beneficial to realize sensing. In addition, JXUST-8 performs relatively good thermal stability, chem. stability, and reusability. Importantly, JXUST-8 could be considered as the first example of a bbip-based MOF as well as the second case of a fluorescence red shifted MOF sensor toward MA. In the experiment, the researchers used many compounds, for example, 2,6-Dibromopyridine(cas: 626-05-1Product Details of 626-05-1)

2,6-Dibromopyridine(cas: 626-05-1) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Product Details of 626-05-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ghiazza, Clement; Faber, Teresa; Gomez-Palomino, Alejandro; Cornella, Josep published an article on January 31 ,2022. The article was titled 《Deaminative chlorination of aminoheterocycles》, and you may find the article in Nature Chemistry.Application In Synthesis of 4-Amino-2-picoline The information in the text is summarized as follows:

Herein we present a simple methodol. that enabled the NH2 groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp2)-NH2 could be converted into C(sp2)-Cl bonds. The method was characterized by its wide functional group tolerance and substrate scope, allowing the modification of different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH2 into Cl in a late-stage fashion enabled practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents. After reading the article, we found that the author used 4-Amino-2-picoline(cas: 18437-58-6Application In Synthesis of 4-Amino-2-picoline)

4-Amino-2-picoline(cas: 18437-58-6) belongs to anime. In organic chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (NH3), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines).Application In Synthesis of 4-Amino-2-picoline

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2002,Organic Syntheses included an article by Smith, Adam P.; Lamba, Jaydeep J. S.; Fraser, Cassandra L.. Application of 138219-98-4. The article was titled 《Efficient synthesis of halomethyl-2,2′-bipyridines: 4,4′-bis(chloromethyl)-2,2′-bipyridine》. The information in the text is summarized as follows:

Silylation of 4,4′-dimethyl-2,2′-bipyridine with LDA followed by chlorotrimethylsilane gave 97% 4,4′-bis(trimethylsilylmethyl)-2,2′-bipyridine, treatment of which with Cl3CCCl3 and CsF in MeCN, gave 91% 4,4′-bis(chloromethyl)-2,2′-bipyridine. Among the 7 other halobipyridines similarly prepared were 98% 5-(chloromethyl)-2,2′-bipyridine 99% 4,4′-bis(bromomethyl)-2,2′-bipyridine. In the experiment, the researchers used 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Application of 138219-98-4)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. 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 of 138219-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2016,ChemMedChem included an article by Doebelin, Christelle; Patouret, Remi; Garcia-Ordonez, Ruben D.; Chang, Mi Ra; Dharmarajan, Venkatasubramanian; Kuruvilla, Dana S.; Novick, Scott J.; Lin, Li; Cameron, Michael D.; Griffin, Patrick R.; Kamenecka, Theodore M.. Formula: C7H8BrNO. The article was titled 《N-Arylsulfonyl Indolines as Retinoic Acid Receptor-Related Orphan Receptor γ (RORγ) Agonists》. The information in the text is summarized as follows:

The nuclear retinoic acid receptor-related orphan receptor γ (RORγ; NR1F3) is a key regulator of inflammatory gene programs involved in T helper 17 (TH17) cell proliferation. As such, synthetic small-mol. repressors (inverse agonists) targeting RORγ have been extensively studied for their potential as therapeutic agents for various autoimmune diseases. Alternatively, enhancing TH17 cell proliferation through activation (agonism) of RORγ may boost an immune response, thereby offering a potentially new approach in cancer immunotherapy. Herein the authors describe the development of N-arylsulfonyl indolines as RORγ agonists. Structure-activity studies reveal a critical linker region in these mols. as the major determinant for agonism. Hydrogen/deuterium exchange coupled to mass spectrometry (HDX-MS) anal. of RORγ-ligand complexes help rationalize the observed results. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)-3-methoxypyridine(cas: 889360-84-3Formula: C7H8BrNO)

2-(Bromomethyl)-3-methoxypyridine(cas: 889360-84-3) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Formula: C7H8BrNO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Koay, Natalie; Tonelli, Devin L.; Truong, Vouy Linh published an article on January 5 ,2011. The article was titled 《Practical and efficient synthesis of N-fused tricyclic indoles》, and you may find the article in Tetrahedron Letters.Formula: C8H9NO3 The information in the text is summarized as follows:

A practical and efficient synthesis of Me 6,7,8,9-tetrahydropyrido[1,2-a]indol-10-ylacetate derivatives is reported. This synthetic approach featured the nucleophilic aromatic substitution of 2-piperidinemethanol derivatives with haloaryl fluorides, and the intramol. Heck coupling as key steps to afford the desired N-fused tricyclic indoles. After reading the article, we found that the author used Methyl 5-methoxypicolinate(cas: 29681-39-8Formula: C8H9NO3)

Methyl 5-methoxypicolinate(cas: 29681-39-8) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Formula: C8H9NO3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2016,Lemouzy, Sebastien; Jean, Marion; Giordano, Laurent; Herault, Damien; Buono, Gerard published 《The Hydroxyalkyl Moiety As a Protecting Group for the Stereospecific Alkylation of Masked Secondary Phosphine-Boranes》.Organic Letters published the findings.Product Details of 31106-82-8 The information in the text is summarized as follows:

The synthesis of functionalized tertiary phosphine-boranes has been developed via a chemodivergent approach from readily accessible (hydroxymethyl) phosphine-boranes under mild conditions. O-Alkylation or decarbonylative P-alkylation product could be exclusively obtained. The P-alkylation reaction was found to proceed in moderate to very good yields and very high enantiospecificity (es >95%) using a variety of alkyl halides as electrophiles. The configurational stability of the sodium phosphido-borane intermediate was also investigated and allowed a deeper understanding of the reaction mechanism, furnishing secondary phosphine-boranes in moderate yield and enantiopurity. In the experimental materials used by the author, we found 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Product Details of 31106-82-8)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) belongs to pyridine. Pyridines form stable salts with strong acids. Pyridine itself is often used to neutralize acid formed in a reaction and as a basic solvent. Product Details of 31106-82-8

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Yamamoto, Yoshihiko; Nishimura, Kei-ichiro; Shibuya, Masatoshi published 《Ruthenium-Catalyzed Cycloisomerization of 1,6-Diynes with Styryl Terminals Leading to Indenylidene Cycloalkanes》.ACS Catalysis published the findings.COA of Formula: C6H4BrNO The information in the text is summarized as follows:

In the presence of a neutral ruthenium catalyst, Cp*RuCl(cod), 1,5,10-enediynes bearing a styryl terminal underwent cycloisomerization to afford exocyclic 1,3-dienes with an indenylidene moiety. The reaction mechanism is proposed on the basis of the results of control experiments and d. functional calculations The transformations of the obtained cyclization products were also investigated to demonstrate the synthetic potential of this method. In addition to this study using 2-Bromonicotinaldehyde, there are many other studies that have used 2-Bromonicotinaldehyde(cas: 128071-75-0COA of Formula: C6H4BrNO) was used in this study.

2-Bromonicotinaldehyde(cas: 128071-75-0) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. COA of Formula: C6H4BrNO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,ChemistrySelect included an article by Lemouzy, Sebastien; Jean, Marion; Deplante, Fabien; Albalat, Muriel; Herault, Damien; Buono, Gerard. Formula: C6H7Br2N. The article was titled 《Tunable P-Stereogenic P,N-Phosphine Ligands Design: Synthesis and Coordination Chemistry to Palladium》. The information in the text is summarized as follows:

The synthesis of P,N heterobidentate phosphine / palladium complexes was realized from P-stereogenic enantiopure ligands. Five, six or seven membered ring complexes were fully characterized, notably by x-ray diffraction, allowing the study of the chelation to a palladium (II) dichloride unit. The nature of nitrogen coordination site as well as the size of the ring modify the bite-angle at the solid state. In the part of experimental materials, we found many familiar compounds, such as 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Formula: C6H7Br2N)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) belongs to pyridine. When pyridine is adsorbed on oxide surfaces or in porous materials, the following species are commonly observed: (i) pyridine coordinated to Lewis acid sites, (ii) pyridine H-bonded to weakly acidic hydroxyls, and (iii) protonated pyridine. At high coverage, physisorbed pyridine and protonated dimers can also be observed.Formula: C6H7Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem