Category: 1692-25-7

Xu, Mizhi; Paul, McKinley K.; Bullard, Krista K.; DuPre, Christopher; Gutekunst, Will R. published an article in 2021. The article was titled 《Modulating Twisted Amide Geometry and Reactivity Through Remote Substituent Effects》, and you may find the article in Journal of the American Chemical Society.SDS of cas: 1692-25-7 The information in the text is summarized as follows:

The unusual reactivity of twisted amides has long been associated with the degree of amide distortion, though classical bridged bicyclic amides offer limited methods to further modify these parameters. Here, we report that the geometry and reactivity of a single twisted amide scaffold can be significantly modulated through remote substituent effects. Guided by calculated ground state geometries, a library of twisted amide derivatives was efficiently prepared through a divergent synthetic strategy. Kinetic and mechanistic investigations of these amides in the alkylation/halide-rebound ring-opening reaction with alkyl halides show a strong pos. correlation between the electron donating ability of the substituent and distortion of the amide bond, leading to rates of nucleophilic substitution spanning nearly 2 orders of magnitude. The rate limiting step of the cascade sequence is found to be dependent on the nature of the substituent, and addnl. studies highlight the role of solvent polarity and halide ion on reaction pathway and efficiency. The experimental part of the paper was very detailed, including the reaction process of Pyridin-3-ylboronic acid(cas: 1692-25-7SDS of cas: 1692-25-7)

Pyridin-3-ylboronic acid(cas: 1692-25-7) 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.SDS of cas: 1692-25-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,Journal of Heterocyclic Chemistry included an article by Heppell, Jacob T.; Islam, Amirul Md.; McAlpine, Shelli R.; Al-Rawi, Jasim M. A.. Synthetic Route of C5H6BNO2. The article was titled 《Functionalization of Quinazolin-4-ones Part 3: Synthesis, Structures Elucidation, DNA-PK, PI3K, and Cytotoxicity of Novel 8-Aryl-2-morpholino-quinazolin-4-ones》. The information in the text is summarized as follows:

A series of novel 8-aryl-2-morpholino quinazolines I (X = H, Cl; Ar = C6H5, 4-ClC6H4, 3-pyridyl, etc.) and II (X = H, Cl; R1 = Me, Bn; Ar = C6H5, 4-MeOC6H4, 3-H2NC6H4, etc.) were synthesized from the precursor 2-thioxo quinazolin-4-one. The compounds I and II were assayed for DNA-dependent protein kinase (DNA-PK) and phosphatidylinositol 3-kinase (PI3K). All compounds showed low DNA-PK % inhibition activity at 10 μM compound concertation, and the compound I (X = H; Ar = dibenzo[b,d]thiophen-4-yl) was most active with 38% inhibition. Similar pattern of PI3K α, β, γ, and δ isoforms inhibition activity at 10 μM were observed and the most active isoform was PI3K δ of 41% inhibition for compound I (X = Cl; Ar = dibenzo[b,d]thiophen-4-yl). Most compounds were less active than expected in spite of the strong structural resemblance to known inhibitors. Loss of activity could be attributed to the tautomerization to the aromatic enol (4-OH), which could specify that the carbonyl (C=O) group is important functional group for the activity. Selected compounds displayed appreciable cytotoxicity and compound I (X = Cl; Ar = dibenzo[b,d]thiophen-4-yl) exhibiting the greatest activity with an IC50 of 9.95 μM, therefore, the mechanism of the cytotoxicity of this compd, were not through DNA-PK or PI3K inhibition activity. The experimental part of the paper was very detailed, including the reaction process of Pyridin-3-ylboronic acid(cas: 1692-25-7Synthetic Route of C5H6BNO2)

Pyridin-3-ylboronic acid(cas: 1692-25-7) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Synthetic Route of C5H6BNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Liu, Zhong; He, Jia-Hao; Zhang, Ming; Shi, Zhu-Jun; Tang, Han; Zhou, Xin-Yue; Tian, Jun-Jie; Wang, Xiao-Chen published an article in Journal of the American Chemical Society. The title of the article was 《Borane-Catalyzed C3-Alkylation of Pyridines with Imines, Aldehydes, or Ketones as Electrophiles》.COA of Formula: C5H6BNO2 The author mentioned the following in the article:

Achieving C3-selective pyridine functionalization is a longstanding challenge in organic chem. The existing methods, including electrophilic aromatic substitution and C-H activation, often require harsh reaction conditions and excess pyridine and generate multiple regioisomers. Herein, authors report a method for borane-catalyzed tandem reactions that result in exclusively C3-selective alkylation of pyridines. These tandem reactions consist of pyridine hydroboration, nucleophilic addition of the resulting dihydropyridine to an imine, an aldehyde, or a ketone, and subsequent oxidative aromatization. Because the pyridine is the limiting reactant and the reaction conditions are mild, this method constitutes a practical tool for late-stage functionalization of structurally complex pharmaceuticals bearing a pyridine moiety. In the experimental materials used by the author, we found Pyridin-3-ylboronic acid(cas: 1692-25-7COA of Formula: C5H6BNO2)

Pyridin-3-ylboronic acid(cas: 1692-25-7) belongs to pyridine. Pyridine’s structure is isoelectronic with that of benzene, but its properties are quite different. Pyridine is completely miscible with water, whereas benzene is only slightly soluble. Like all hydrocarbons, benzene is neutral (in the acid–base sense), but because of its nitrogen atom, pyridine is a weak base.COA of Formula: C5H6BNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Name: Pyridin-3-ylboronic acidIn 2019 ,《A Mild and Direct Site-Selective sp2 C-H Silylation of (Poly)Azines》 was published in Journal of the American Chemical Society. The article was written by Gu, Yiting; Shen, Yangyang; Zarate, Cayetana; Martin, Ruben. The article contains the following contents:

A base-mediated protocol that allows for the site-selective sp2 C-H silylation of pyridines, pyrazines, pyridazines, pyrimidines and quinolines by Et3SiBpin is described. The substitution typically proceeds in 4- or 2-position of the pyridine ring. This method is distinguished by its mild conditions, simplicity and excellent site-selective modulation for a diverse set of azines, even in the context of late-stage functionalization, while exhibiting orthogonal reactivity with classical silylation reactions.Pyridin-3-ylboronic acid(cas: 1692-25-7Name: Pyridin-3-ylboronic acid) was used in this study.

Pyridin-3-ylboronic acid(cas: 1692-25-7) 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. Name: Pyridin-3-ylboronic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Name: Pyridin-3-ylboronic acidIn 2020 ,《Novel, Potent, and Druglike Tetrahydroquinazoline Inhibitor That Is Highly Selective for Human Topoisomerase II α over β》 was published in Journal of Medicinal Chemistry. The article was written by Ortega, Jose Antonio; Arencibia, Jose M.; Minniti, Elirosa; Byl, Jo Ann W.; Franco-Ulloa, Sebastian; Borgogno, Marco; Genna, Vito; Summa, Maria; Bertozzi, Sine Mandrup; Bertorelli, Rosalia; Armirotti, Andrea; Minarini, Anna; Sissi, Claudia; Osheroff, Neil; De Vivo, Marco. The article contains the following contents:

We disclose a novel class of 6-amino-tetrahydroquinazoline derivatives that inhibit human topoisomerase II (topoII), a validated target of anticancer drugs. In contrast to topoII-targeted drugs currently in clin. use, these compounds do not act as topoII poisons that enhance enzyme-mediated DNA cleavage, a mechanism that is linked to the development of secondary leukemias. Instead, these tetrahydroquinazolines block the topoII function with no evidence of DNA intercalation. We identified a potent lead compound [compound I (ARN-21934) IC50 = 2μM for inhibition of DNA relaxation, as compared to an IC50 = 120μM for the anticancer drug etoposide] with excellent metabolic stability and solubility This new compound also shows ∼100-fold selectivity for topoIIα over topoβ, a broad antiproliferative activity toward cultured human cancer cells, a favorable in vivo pharmacokinetic profile, and the ability to penetrate the blood-brain barrier. Thus, ARN-21934 is a highly promising lead for the development of novel and potentially safer topoII-targeted anticancer drugs. The experimental part of the paper was very detailed, including the reaction process of Pyridin-3-ylboronic acid(cas: 1692-25-7Name: Pyridin-3-ylboronic acid)

Pyridin-3-ylboronic acid(cas: 1692-25-7) 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. Name: Pyridin-3-ylboronic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of C5H6BNO2In 2020 ,《Organoboron-Functionalization Enables the Hierarchical Assembly of Giant Polyoxometalate Nanocapsules》 was published in Angewandte Chemie, International Edition. The article was written by Li, Shujun; Zhou, Yanfang; Ma, Nana; Zhang, Jie; Zheng, Zhiping; Streb, Carsten; Chen, Xuenian. The article contains the following contents:

The aggregation of mol. metal oxides into larger superstructures can bridge the gap between mol. compounds and solid-state materials. Here, we report that functionalization of polyoxotungstates with organo-boron substituents leads to giant polyoxometalate-based nanocapsules with dimensions of up to 4 nm. A “”lock and key”” mechanism enables the site-specific anchoring of aromatic organo-boronic acids to metal-functionalized Dawson anions [M3P2W15O62]9- (M = TaV or NbV), resulting in unique nanocapsules containing up to twelve POM units. Exptl. and theor. studies provide initial insights into the role of the organo-boron moieties and the metal-functionalized POMs for the assembly of the giant aggregates. The study therefore lays the foundations for the design of organo-POM-based functional nanostructures. In the experiment, the researchers used Pyridin-3-ylboronic acid(cas: 1692-25-7Electric Literature of C5H6BNO2)

Pyridin-3-ylboronic acid(cas: 1692-25-7) 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 C5H6BNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,Physical Chemistry Chemical Physics included an article by Iribarren, Inigo; Montero-Campillo, M. Merced; Alkorta, Ibon; Elguero, Jose; Quinonero, David. SDS of cas: 1692-25-7. The article was titled 《Cations brought together by hydrogen bonds: the protonated pyridine-boronic acid dimer explained》. The information in the text is summarized as follows:

According to the Cambridge Structural Database, protonated pyridine-boronic acid dimers exist in the solid phase, apparently defying repulsive coulombic forces. In order to understand why these cation-cation systems are stable, we carried out M06-2X/6-311++G(3df,2pd) electronic structure calculations and used a set of computational tools (energy partitioning, topol. of the electron d. and elec. field maps). The behavior of the charged dimers was compared with the corresponding neutral systems, and the effect of counterions (Br- and BF4-) and the solvent (PCM model) on the binding energies has been considered. In the gas-phase, the charged dimers present pos. binding energies but are local min., with a barrier (16-19 kJ mol-1) preventing dissociation Once the environment is included via solvent effects or counterions, the binding energies become neg.; remarkably, the strength of the interaction is very similar in both neutral and charged systems when a polar solvent is considered. Essentially, all methods used evidence that the intermol. region where the HBs take place is very similar for both neutral and charged dimers. The energy partitioning explains that repulsion and electrostatic terms are compensated by the desolvation and exchange terms in polar solvents, thus giving stability to the charged dimer.Pyridin-3-ylboronic acid(cas: 1692-25-7SDS of cas: 1692-25-7) was used in this study.

Pyridin-3-ylboronic acid(cas: 1692-25-7) belongs to pyridine. Pyridine’s structure is isoelectronic with that of benzene, but its properties are quite different. Pyridine is completely miscible with water, whereas benzene is only slightly soluble. Like all hydrocarbons, benzene is neutral (in the acid–base sense), but because of its nitrogen atom, pyridine is a weak base.SDS of cas: 1692-25-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Guo, Zhewen; Li, Guangfeng; Wang, Heng; Zhao, Jun; Liu, Yuhang; Tan, Hongwei; Li, Xiaopeng; Stang, Peter J.; Yan, Xuzhou published an article in 2021. The article was titled 《Drum-like Metallacages with Size-Dependent Fluorescence: Exploring the Photophysics of Tetraphenylethylene under Locked Conformations》, and you may find the article in Journal of the American Chemical Society.Electric Literature of C5H6BNO2 The information in the text is summarized as follows:

Materials with aggregation-induced emission (AIE) properties are of growing interest due to their widespread applications. AIEgens, such as tetraphenylethylene units, display varying emission behaviors during their conformational changes. However, the structure-property relationships of the intermediate conformations have rarely been explored. Herein, the authors show that the conformational restriction on TPE units can affect the structural relaxation in the excited state and the resulting photophys. behaviors. Specifically, three metallacages of different sizes were prepared via the coordination-driven self-assembly of a TPE-based tetrapyridyl donor with length-increasing Pt(II) acceptors. While the metallacages share similar scaffolds, they exhibit a trend of red-shifted fluorescence and attenuated quantum yield with the increase of their sizes. Furthermore, spectroscopic and computational studies together with a control experiment were conducted, revealing that the degree of cage tension imposed on the excited-state conformational relaxation of TPE moieties resulted in their distinct photophys. properties. The precise control of conformation holds promise as a strategy for understanding the AIE mechanism as well as optimizing the photophys. behaviors of materials on the platform of supramol. coordination complexes. After reading the article, we found that the author used Pyridin-3-ylboronic acid(cas: 1692-25-7Electric Literature of C5H6BNO2)

Pyridin-3-ylboronic acid(cas: 1692-25-7) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.Electric Literature of C5H6BNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Wu, Terence; Tatton, Matthew R.; Greaney, Michael F. published an article in Angewandte Chemie, International Edition. The title of the article was 《NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy-Breslow Intermediates》.Safety of Pyridin-3-ylboronic acid The author mentioned the following in the article:

Umpolung N-heterocyclic carbene (NHC) catalysis of non-aldehyde substrates offers new pathways for CC bond formation, but has proven challenging to develop in terms of viable substrate classes. Here, the authors demonstrate that pyridinium ions can undergo NHC addition and subsequent intramol. C-C bond formation through a deoxy-Breslow intermediate. The alkylation demonstrates, for the first time, that deoxy-Breslow intermediates are viable for catalytic umpolung of areniums. In the part of experimental materials, we found many familiar compounds, such as Pyridin-3-ylboronic acid(cas: 1692-25-7Safety of Pyridin-3-ylboronic acid)

Pyridin-3-ylboronic acid(cas: 1692-25-7) 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. Safety of Pyridin-3-ylboronic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Upadhyay, Rahul; Singh, Deepak; Maurya, Sushil K. published an article in 2021. The article was titled 《Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols》, and you may find the article in European Journal of Organic Chemistry.Quality Control of Pyridin-3-ylboronic acid The information in the text is summarized as follows:

A V2O5@TiO2 catalyzed green and efficient protocol for hydroxylation of boronic acid into phenol was developed utilizing environmentally benign oxidant hydrogen peroxide. A wide range of electron-donating and electron-withdrawing group-containing (hetero)aryl boronic acids were transformed into their corresponding phenol. The methodol. was also applied successfully to transform various natural and bioactive mols. like tocopherol, amino acids, cinchonidine, vasicinone, menthol and pharmaceuticals such as ciprofloxacin, ibuprofen and paracetamol. The other feature of methodol. included gram-scale synthetic applicability, recyclability and short reaction time. The experimental process involved the reaction of Pyridin-3-ylboronic acid(cas: 1692-25-7Quality Control of Pyridin-3-ylboronic acid)

Pyridin-3-ylboronic acid(cas: 1692-25-7) belongs to pyridine. Pyridine derivatives lend themselves to many roles in the spirited field of supramolecular chemistry – whether as the ligand backbone of metal-organic polymers or presiding over the key electronic stations of nanodevices. In biochemistry, pyridine-containing cofactors are necessary nutrients on which our lives depend. Quality Control of Pyridin-3-ylboronic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem