Day: November 8, 2022

In 2008,Martin, Thibaut; Verrier, Cecile; Hoarau, Christophe; Marsais, Francis published 《Direct C-2 arylation of alkyl 4-thiazolecarboxylates: new insights in synthesis of heterocyclic core of thiopeptide antibiotics》.Organic Letters published the findings.Application of 29682-15-3 The information in the text is summarized as follows:

The Pd(0)-catalyzed regioselective C-2 (hetero)arylation of tert-Bu 4-thiazolecarboxylate with a broad (hetero)aryl halide is reported, including the direct coupling of pyridinyl halides. The process has allowed the preparation of valuable 2-pyridynyl-4-thiazolecarboxylates which are components of the complex heterocyclic core of thiopeptides antibiotics. As a first application, a synthesis of a tert-Bu sulfomycinamate thio-analog from tert-Bu 4-thiazolecarboxylate is here described through a three-step direct pyridinylation, halogenation, and Stille cross-coupling sequence.Methyl 5-bromopicolinate(cas: 29682-15-3Application of 29682-15-3) was used in this study.

Methyl 5-bromopicolinate(cas: 29682-15-3) 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.Application of 29682-15-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2014,Kundu, Debasish; Ahammed, Sabir; Ranu, Brindaban C. published 《Visible Light Photocatalyzed Direct Conversion of Aryl-/Heteroarylamines to Selenides at Room Temperature》.Organic Letters published the findings.Related Products of 13534-97-9 The information in the text is summarized as follows:

A novel strategy for the direct conversion of aryl- and heteroarylamines to selenides has been developed via diazotization of amines with tert-Bu nitrite in neutral medium followed by reaction with diaryl/diheteroaryl/dialkyl diselenides in one pot under photocatalysis at room temperature in the absence of any metal. This reaction is also applied for the synthesis of tellurides. The selenylation of heteroarylamine by this protocol is of much significance because of the difficulty in diazotization of these mols. by a standard diazotization method in acid medium. The results came from multiple reactions, including the reaction of 6-Bromopyridin-3-amine(cas: 13534-97-9Related Products of 13534-97-9)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Related Products of 13534-97-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2014,Wagner, Patrick; Bollenbach, Maud; Doebelin, Christelle; Bihel, Frederic; Bourguignon, Jean-Jacques; Salome, Christophe; Schmitt, Martine published 《t-BuXPhos: a highly efficient ligand for Buchwald-Hartwig coupling in water》.Green Chemistry published the findings.Electric Literature of C5H3BrClN The information in the text is summarized as follows:

An efficient and versatile ‘green’ catalytic system for the Buchwald-Hartwig cross-coupling reaction in water is reported. In an aqueous micellar medium, the combination of t-BuXPhos with [(cinnamyl)PdCl]2 showed excellent performance for coupling of aryl bromides or chlorides with a large set of amines, amides, ureas, and carbamates. The method is functional-group tolerant, proceeds smoothly (30 to 50 °C), and provides rapid access to the target compounds in good to excellent isolated yields. When applied to the synthesis of a known NaV1.8 modulator, this method led to a significant improvement of the E-factor in comparison with classical organic synthesis. In the experiment, the researchers used many compounds, for example, 5-Bromo-2-chloropyridine(cas: 53939-30-3Electric Literature of C5H3BrClN)

5-Bromo-2-chloropyridine(cas: 53939-30-3) 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.Electric Literature of C5H3BrClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2015,Nakae, Toyotaka; Hirotsu, Masakazu; Kinoshita, Isamu published 《Di- and mononuclear iron complexes of N,C,S-tridentate ligands containing an aminopyridyl group: effect of the pendant amine site on catalytic properties for proton reduction》.Organometallics published the findings.Formula: C5H5BrN2 The information in the text is summarized as follows:

A series of diiron complexes of N,C,S-tridentate ligands containing a 6-, 5-, or 4-amino-2-pyridyl group, [{Fe(μ-L-κ3N,C,S)(CO)2}Fe(CO)3] [2, L = o-apyBPT; 3, L = m-apyBPT; 4, L = p-apyBPT; apyBPT = 2-(2-aminopyridinyl)-6-(2-phenylthiolato)phenyl-κC1,κN,κS], was prepared Complexes 2-4 were converted to the mononuclear iron(II) complexes trans-[Fe(L-κ3N,C,S)(CO)(PMe2Ph)2] (6, L = o-apyBPT; 7, L = m-apyBPT; 8, L = p-apyBPT). In 2 and 6, the o-amino group is close to Fe bound to the aminopyridyl group. Cyclic voltammograms of 2-4 exhibit two consecutive one-electron reduction events, and catalytic current for proton reduction appears in the presence of acetic acid. The reduction potentials of 2-4 are similar to each other, while the overpotential for proton reduction with o-amino complex 2 is ca. 0.2 V lower than those with 3 and 4. In the mononuclear complexes 6-8, the redox potentials for the FeIII/FeII couple are dependent on the position of the amino group in the pyridine ring, which is described by electronic and steric effects of the amino group. Such effects on the redox potentials are suppressed in the diiron complexes because the reduction occurs at the diiron core with π-accepting CO ligands, which is supported by DFT calculations The lower overpotential in 2 compared with 3 and 4 is attributed to the concerted effect of the amino group proximal to the iron center. The amino group probably acts as a proton acceptor and assists the formation of the H-H bond from a hydride on the iron centers and a proton bound to the amino group. In the experiment, the researchers used many compounds, for example, 6-Bromopyridin-3-amine(cas: 13534-97-9Formula: C5H5BrN2)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Formula: C5H5BrN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2016,Huang, Liangbin; Weix, Daniel J. published 《Ruthenium-Catalyzed C-H Arylation of Diverse Aryl Carboxylic Acids with Aryl and Heteroaryl Halides》.Organic Letters published the findings.Safety of 5-Bromo-2-chloropyridine The information in the text is summarized as follows:

Ruthenium ligated to tricyclohexylphosphine or di-tert-butylbipyridine catalyzes the arylation of carboxylic acids with diverse aryl halides (iodide, bromide, and triflate; aryl and heteroaryl). In addition, arylations with 2-iodophenol formed benzochromenones, carboxylate was shown to be a stronger donor than an amide, and the arylation of a pyridine carboxylate was demonstrated. Stoichiometric studies demonstrated that the added ligand is required for reaction with the electrophile but not the C-H bond. After reading the article, we found that the author used 5-Bromo-2-chloropyridine(cas: 53939-30-3Safety of 5-Bromo-2-chloropyridine)

5-Bromo-2-chloropyridine(cas: 53939-30-3) 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.Safety of 5-Bromo-2-chloropyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Biochemistry included an article by Hinchliffe, Philip; Tanner, Carol A.; Krismanich, Anthony P.; Labbe, Genevieve; Goodfellow, Valerie J.; Marrone, Laura; Desoky, Ahmed Y.; Calvopina, Karina; Whittle, Emily E.; Zeng, Fanxing; Avison, Matthew B.; Bols, Niels C.; Siemann, Stefan; Spencer, James; Dmitrienko, Gary I.. Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromide. The article was titled 《Structural and Kinetic Studies of the Potent Inhibition of Metallo-β-lactamases by 6-Phosphonomethylpyridine-2-carboxylates》. The information in the text is summarized as follows:

There are currently no clin. available inhibitors of metallo-β-lactamases (MBLs), enzymes which hydrolyze β-lactam antibiotics and confer resistance on Gram-neg. bacteria. Here we present 6-phosphonomethylpyridine-2-carboxylates (PMPCs) as potent inhibitors of subclass B1 (IMP-1, VIM-2, NDM-1) and B3 (L1) MBLs. Inhibition followed a competitive, slow-binding model without an isomerization step (IC50 values 0.3 – 7.2 μM; Ki 0.03 – 1.5 μM). Min. inhibitory concentration assays demonstrated potentiation of β-lactam (meropenem) activity against MBL-producing bacteria, including clin. isolates, at concentrations where eukaryotic cells remain viable. Crystal structures revealed unprecedented modes of inhibitor binding to B1 (IMP-1) and B3 (L1) MBLs. In IMP-1, binding does not replace the nucleophilic hydroxide and the PMPC carboxylate and pyridine nitrogen interact closely (2.3 and 2.7 Å, resp.) with the Zn2 ion of the binuclear metal site. The phosphonate group makes limited interactions, but is 2.6 Å from the nucleophilic hydroxide. Furthermore, the presence of a water mol. interacting with the PMPC phosphonate and pyridine N-C2 π-bond, as well as the nucleophilic hydroxide, suggests that the PMPC binds to the MBL active site as its hydrate. Binding is markedly different in L1, with the phosphonate displacing both Zn2, forming a monozinc enzyme, and the nucleophilic hydroxide, while also making multiple interactions with the protein main chain and Zn1. The carboxylate and pyridine nitrogen interact with Ser221/223, resp. (3 Å distance). The potency, low toxicity, cellular activity and amenability to further modification of PMPCs indicate these and similar phosphonate compounds can be further considered for future MBL inhibitor development. The experimental process involved the reaction of 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromide)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) 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. Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,Journal of Bacteriology included an article by Qiu, Jiguo; Zhao, Lingling; Xu, Siqiong; Chen, Qing; Chen, Le; Liu, Bin; Hong, Qing; Lu, Zhenmei; He, Jian. Name: Picolinic acid. The article was titled 《Identification and characterization of a novel pic gene cluster responsible for picolinic acid degradation in Alcaligenes faecalis JQ135》. The information in the text is summarized as follows:

Picolinic acid (PA) is a natural toxic pyridine derivative Microorganisms can degrade and utilize PA for growth. However, the full catabolic pathway of PA and its physiol. and genetic foundation remain unknown. In this study, we identified a gene cluster, designated picRCEDFB4B3B2B1A1A2A3, responsible for the degradation of PA from Alcaligenes faecalis JQ135. Our results suggest that PA degradation pathway occurs as follows: PA was initially 6-hydroxylated to 6-hydroxypicolinic acid (6HPA) by PicA (a PA dehydrogenase). 6HPA was then 3-hydroxylated by PicB, a four-component 6HPA monooxygenase, to form 3,6-dihydroxypicolinic acid (3,6DHPA), which was then converted into 2,5-dihydroxypyridine (2,5DHP) by the decarboxylase PicC. 2,5DHP was further degraded to fumaric acid through PicD (2,5DHP 5,6-dioxygenase), PicE (N-formylmaleamic acid deformylase), PicF (maleamic acid amidohydrolase), and PicG (maleic acid isomerase). Homologous pic gene clusters with diverse organizations were found to be widely distributed in Alpha-, Beta-, and Gammaproteobacteria. Our findings provide new insights into the microbial catabolism of environmental toxic pyridine derivatives IMPORTANCE Picolinic acid is a common metabolite of L-tryptophan and some aromatic compounds and is an important intermediate in organic chem. synthesis. Although the microbial degradation/detoxification of picolinic acid has been studied for over 50 years, the underlying mol. mechanisms are still unknown. Here, we show that the pic gene cluster is responsible for the complete degradation of picolinic acid. The pic gene cluster was found to be widespread in other Alpha-, Beta-, and Gammaproteobacteria. These findings provide a new perspective for understanding the catabolic mechanisms of picolinic acid in bacteria. The results came from multiple reactions, including the reaction of Picolinic acid(cas: 98-98-6Name: Picolinic acid)

Picolinic acid(cas: 98-98-6) is used in the preparation of 2-Aminodihydro[1,3]thiazines as BACE 2 inhibitors and their preparation and use in the treatment of diabetes.Name: Picolinic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,Green Chemistry included an article by Yamada, Makito; Shio, Yasunori; Akiyama, Toshiki; Honma, Tetsuo; Ohki, Yuuta; Takahashi, Naoyuki; Murai, Kenichi; Arisawa, Mitsuhiro. Computed Properties of C5H6BNO2. The article was titled 《Ligand-free Suzuki-Miyaura coupling reaction of aryl chlorides using a continuous irradiation type microwave and a palladium nanoparticle catalyst: effect of a co-existing solid》. The information in the text is summarized as follows:

The effect of a co-existing metal in the ligand-free Suzuki-Miyaura coupling reaction of aryl chlorides ArCl (Ar = Ph, pyridin-2-yl, naphthalen-1-yl, etc.) is promoted by a ”continuous irradiation type microwave” and a ”palladium nanoparticle catalyst”, and it is found that the co-existing metal affects this reaction due to its absorption ability of microwave energy in the reaction system. It is also observed that spiking occurred more frequently in the presence of a co-existing metal. In the part of experimental materials, we found many familiar compounds, such as 2-Pyridinylboronic acid(cas: 197958-29-5Computed Properties of C5H6BNO2)

2-Pyridinylboronic acid(cas: 197958-29-5) 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.Computed Properties of C5H6BNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,Nanomaterials included an article by Lopez-Tocon, Isabel; Valdivia, Samuel; Soto, Juan; Otero, Juan Carlos; Muniz-Miranda, Francesco; Menziani, Maria Cristina; Muniz-Miranda, Maurizio. Recommanded Product: 100-48-1. The article was titled 《A DFT approach to the surface-enhanced Raman scattering of 4-cyanopyridine adsorbed on silver nanoparticles》. The information in the text is summarized as follows:

A Surface-Enhanced Raman Scattering (SERS) spectrum of 4-cyanopyridine (4CNPy) was recorded on silver plasmonic nanoparticles and analyzed by using D. Functional Theory (DFT) calculations Two simple mol. models of the metal-4CNPy surface complex with a single silver cation or with a neutral dimer (Ag+-4CNPy, Ag2-4CNPy), linked through the two possible interacting sites of 4CNPy (aromatic nitrogen, N, and nitrile group, CN), were considered. The calculated vibrational wavenumbers and intensities of the adsorbate and the isolated species are compared with the exptl. Raman and SERS results. The anal. of the DFT predictions and the exptl. data indicates that 4CNPy adsorbs preferentially on neutral/charged active sites of the silver nanoparticles through the nitrogen atom of the aromatic ring with a perpendicular orientation. After reading the article, we found that the author used 4-Cyanopyridine(cas: 100-48-1Recommanded Product: 100-48-1)

4-Cyanopyridine(cas: 100-48-1) 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. Recommanded Product: 100-48-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《Molecular design and structural pecularities of the 3- and 4-pyridylboron-capped tris-glyoximate and tris-dichloroglyoximate iron(II) clathrochelates with apical donor groups》 were Zelinskii, Genrikh E.; Belov, Alexander S.; Vologzhanina, Anna V.; Limarev, Ilya P.; Dorovatovskii, Pavel V.; Zubavichus, Yan V.; Lebed, Ekaterina G.; Voloshin, Yan Z.; Dedov, Alexey G.. And the article was published in Polyhedron in 2019. Reference of Pyridin-3-ylboronic acid The author mentioned the following in the article:

Tris-glyoximate and tris-dichloroglyoximate iron(II) clathrochelates with apical pyridyl groups were obtained through one-pot template condensation of the corresponding α-dioxime with 3- or 4-pyridylboronic acids on the iron(II) ion as a matrix under vigorous reaction conditions using the boiling CF3COOH as a solvent. The initially formed mixtures of mono- and diprotonated clathrochelate species were converted into the target macrobicyclic intracomplexes under basic conditions. These complexes were characterized using elemental anal., MALDI-TOF mass spectrometry, IR, UV-visible, 1H and 13C NMR spectroscopies, and by single crystal x-ray diffraction as well. In their mols., the encapsulated iron(II) ion is situated in the center of its FeN6-coordination polyhedron. The geometry of all the FeN6-coordination polyhedra is intermediate between a trigonal prism and a trigonal antiprism with the average distortion angles φ from 16.7 to 17.7°. Their heights h fall from 2.36 to 2.38 Å and the averaged bite angles α vary in a narrow range 78.2-78.4°. Characteristic feature of the 3- and 4-pyridylboron-capped glyoximate clathrochelate mols., as compared with their aliphatic and aromatic analogs, is shortening of the chelate C-C bonds from 1.45 to 1.42 Å. Comparison of the values of a ligand aspect ratio for the obtained new pyridyl-terminated iron(II) clathrochelates with those for their known aliphatic tris-dioximate analogs was performed. After reading the article, we found that the author used Pyridin-3-ylboronic acid(cas: 1692-25-7Reference 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. Reference of Pyridin-3-ylboronic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem