Month: October 2022

Nakamura, Takashi; Yonemura, Sota; Akatsuka, Shunya; Nabeshima, Tatsuya published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Synthesis of Single Isomeric Complexes with Dissymmetric Structures Using Macrocyclic Homooligomers》.Application of 3510-66-5 The article contains the following contents:

Bottom-up chem. synthesis to construct intricate mols. is a profound challenge. An effective approach is to use organic ligands and metal ions, but the formation of a single product among other possible candidates proved difficult for dissym. structures. The authors now report the synthesis of single isomeric complexes with dissym. structures using the mismatch in the coordination valences of macrocyclic homooligomers and metal ions. Amide-cyclodextrin derivatives possessing multiple 2,2′-bipyridyl (bpy) groups forms mononuclear complexes whose specific three bpy groups are linked in the fac-Λ configuration. The intermol. coordination of the β-cyclodextrin metal complex produces a dissym. cyclodextrin trimer as a single isomer, whose initially equivalent 21 (7×3) bipyridylamide-pyranose units are placed in different environments. Also, the authors realize chiral recognition of amino acid anions using the distinctive amide groups arranged on the unsym. fixed scaffold. The results came from multiple reactions, including the reaction of 2-Bromo-5-methylpyridine(cas: 3510-66-5Application of 3510-66-5)

2-Bromo-5-methylpyridine(cas: 3510-66-5) belongs to pyridine. Pyridines are often used as catalysts or reagents; particular notice has been paid recently to how pyridine coordinates to metal centers enabling a wide range of valuable reactions. Application of 3510-66-5

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Harnying, Wacharee; Sudkaow, Panyapon; Biswas, Animesh; Berkessel, Albrecht published an article in 2021. The article was titled 《N-Heterocyclic Carbene/Carboxylic Acid Co-Catalysis Enables Oxidative Esterification of Demanding Aldehydes/Enals, at Low Catalyst Loading》, and you may find the article in Angewandte Chemie, International Edition.SDS of cas: 103-74-2 The information in the text is summarized as follows:

The discovery that simple carboxylic acids, such as benzoic acid, boost the activity of N-heterocyclic carbene (NHC) catalysts in the oxidative esterification of aldehydes RCHO (R = heptan-3-yl, Ph, 1-[4-(propan-2-yl)phenyl]propan-2-yl, 6-methylhept-5-en-2-yl, etc.) was reported. A simple and efficient protocol for the transformation of a wide range of sterically hindered α- and β-substituted aliphatic aldehydes/enals, catalyzed by a novel and readily accessible N-Mes-/N-2,4,6-trichlorophenyl 1,2,4-triazolium salt, and benzoic acid as co-catalyst, was developed. A whole series of α/β-substituted aliphatic aldehydes/enals hitherto not amenable to NHC-catalyzed esterification could be reacted at typical catalyst loadings of 0.02-1.0 mol%. For benzaldehyde, even 0.005 mol% of NHC catalyst proved sufficient: the lowest value ever achieved in NHC catalysis. Preliminary studies point to carboxylic acid-induced acceleration of acyl transfer from azolium enolate intermediates as the mechanistic basis of the observed effect.2-(2-Hydroxyethyl)pyridine(cas: 103-74-2SDS of cas: 103-74-2) was used in this study.

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) 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. SDS of cas: 103-74-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Antoni, Patrick W.; Golz, Christopher; Hansmann, Max M. published an article in Angewandte Chemie, International Edition. The title of the article was 《Organic Four-Electron Redox Systems Based on Bipyridine and Phenanthroline Carbene Architectures》.Safety of 2,6-Dibromopyridine The author mentioned the following in the article:

Novel organic redox systems that display multistage redox behavior are highly sought-after for a series of applications such as organic batteries or electrochromic materials. Here we describe a simple strategy to transfer well-known two-electron redox active bipyridine and phenanthroline architectures into novel strongly reducing four-electron redox systems featuring fully reversible redox events with up to five stable oxidation states. We give spectroscopic and structural insight into the changes involved in the redox-events and present characterization data on all isolated oxidation states. The redox-systems feature strong UV/Vis/NIR polyelectrochromic properties such as distinct strong NIR absorptions in the mixed valence states. Two-electron charge-discharge cycling studies indicate high electrochem. stability at strongly neg. potentials, rendering the new redox architectures promising lead structures for multi-electron anolyte materials. The experimental part of the paper was very detailed, including the reaction process of 2,6-Dibromopyridine(cas: 626-05-1Safety of 2,6-Dibromopyridine)

2,6-Dibromopyridine(cas: 626-05-1) 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.Safety of 2,6-Dibromopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Voelkel, Martin H. H.; Engelage, Elric; Kondratiuk, Mykhailo; Huber, Stefan M. published an article in European Journal of Organic Chemistry. The title of the article was 《Evaluation of 6-Halogenated 2-Pyridone Moieties as Halogen Bond Donors》.Safety of 2,6-Dibromopyridine The author mentioned the following in the article:

6-Halo-2-pyridones and their pyridol tautomers show different grades of polarization on their halogen substituents in DFT calculations This and the fact that the tautomeric equilibrium was affected by the surrounding medium make them interesting candidates for a new platform of halogen bond donors. Therefore four simple halopyridones was probed for their halogen bonding properties both in the solid state and in solution Concurring with hydrogen bonding, halogen bonding indeed was found to be an interaction governing the packing motif in pyridone crystals, which was more pronounced in N-methylated congeners. Solution studies using a halide abstraction reaction and NMR titrations against bromide salts, however, showed no clear evidence for halogen bonding in solution After reading the article, we found that the author used 2,6-Dibromopyridine(cas: 626-05-1Safety of 2,6-Dibromopyridine)

2,6-Dibromopyridine(cas: 626-05-1) 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 2,6-Dibromopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Cesari, Andrea; Casulli, Maria Antonietta; Hashimoto, Takeshi; Hayashita, Takashi published an article in International Journal of Molecular Sciences. The title of the article was 《NMR Investigation of the Supramolecular Complex Formed by a Phenylboronic Acid-Ferrocene Electroactive Probe and Native or Derivatized β-Cyclodextrin》.Category: pyridine-derivatives The author mentioned the following in the article:

Specifically designed electrochem. sensors are standing out as alternatives to enzyme-based biosensors for the sensing of metabolites. In our previous works, we developed a new electrochem. assay based on cyclodextrin supramol. complexes. A ferrocene moiety (Fc) was chem. modified by phenylboronic acid (4-Fc-PB) and combined with two different kinds of cyclodextrins (CDs): β-CD and β-CD modified by a dipicolylamine group (dpa-p-HB-β-CDs) for the sensing of fructose and adenosine-triphosphate (ATP), resp. The aim of the present work is to better comprehend the features underlining the aforementioned complex formation. For the first time, a study about inclusion phenomena between the 4-Fc-PB electroactive probe with β-CD and with dpa-p-HB-β-CD was performed by using NMR (NMR) anal. In particular, we focused on providing insights on the interaction involved and on the calculation of the binding constant of 4-Fc-PB/β-CD supramol. complex, and elucidation about a drift in the time observed during the control experiments of the electrochem. measurements for the 4-Fc-PB/dpa-p-HB-β-CD supramol. complex. In this sense, this paper represents a step further in the explanation of the electrochem. results obtained, pointing out the nature of the interactions present both in the formation of the inclusions and in the sensing with the analytes. In the experiment, the researchers used Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0Category: pyridine-derivatives)

Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0) is a secondary amine with two picolyl substituents. The compound is a tridentate ligand in coordination chemistry and commonly used to produce Zn-based chemosensors/probes, such as Zinpry.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

HPLC of Formula: 29682-15-3In 2010 ,《Towards the synthesis of substituted porphyrins with a pyridyl group bearing a reactive functionality》 appeared in Journal of Porphyrins and Phthalocyanines. The author of the article were El Ojaimi, Maya; Habermeyer, Benoit; Gros, Claude P.; Barbe, Jean-Michel. The article conveys some information:

Pyridyl-substituted porphyrins bearing a reactive functionality were prepared via Suzuki cross-coupling reactions and resulted in very good yields. These compounds are precursors of new porphyrin architectures able to coordinate two metals: one in the porphyrin core and the second around the pyridyl moiety. During the coupling reactions, a higher reactivity of a chloro picolyl group was evidenced compared to a bromo function on the same reacting mol. In the experiment, the researchers used Methyl 5-bromopicolinate(cas: 29682-15-3HPLC of Formula: 29682-15-3)

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

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of C7H6BrNO2In 2014 ,《Synthesis and Late-Stage Functionalization of Complex Molecules through C-H Fluorination and Nucleophilic Aromatic Substitution》 appeared in Journal of the American Chemical Society. The author of the article were Fier, Patrick S.; Hartwig, John F.. The article conveys some information:

The authors report the late-stage functionalization of multisubstituted pyridines and diazines at the position α to nitrogen. By this process, functional groups and substituents bound to the ring through nitrogen, oxygen, sulfur, or carbon are installed. This functionalization is accomplished by a combination of fluorination and nucleophilic aromatic substitution of the installed fluoride. A diverse array of functionalities can be installed because of the mild reaction conditions revealed for nucleophilic aromatic substitutions (SNAr) of the 2-fluoroheteroarenes. An evaluation of the rates for substitution vs. the rates for competitive processes provides a framework for planning this functionalization sequence. This process is illustrated by the modification of medicinally important compounds, as well as the increase in efficiency of synthesis of several existing pharmaceuticals. After reading the article, we found that the author used Methyl 5-bromopicolinate(cas: 29682-15-3Synthetic Route of C7H6BrNO2)

Methyl 5-bromopicolinate(cas: 29682-15-3) belongs to pyridine. The basicity and metallophilic high donor number of these π-deficient systems has long favored them as ligands in metal catalysis. The last decade saw pyridine assume a stronger role as functional group for directed C–H oxidation/activation.Synthetic Route of C7H6BrNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of Pyridin-3-ylboronic acidIn 2022 ,《Synthesis of pyrazolo[1,5-a]pyrimidine ring as a possible bioisosteric replacement of the 5-(1H-pyrrol-1-yl)pyrazole scaffold》 appeared in ARKIVOC (Gainesville, FL, United States). The author of the article were Mugnaini, Claudia; Pasculini, Livia; Pagli, Carlotta; Brizzi, Antonella; Paolino, Marco; Gianibbi, Beatrice; Corelli, Federico. The article conveys some information:

Reaction of 3-amino-1H-pyrazole-4-carbonitrile with 2,4-pentanedione yielded 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carbonitrile, which was easily and efficiently transformed into a small library of amido derivatives I (R = 4-bromophenyl, 6-chloropyridin-3-yl, 6-(pyridin-3-yl)pyridin-3-yl, etc.). This procedure opens the way to new compounds potentially endowed with interesting biol. activities. The experimental part of the paper was very detailed, including the reaction process of Pyridin-3-ylboronic acid(cas: 1692-25-7Reference of Pyridin-3-ylboronic acid)

Pyridin-3-ylboronic acid(cas: 1692-25-7) belongs to pyridine. The basicity and metallophilic high donor number of these π-deficient systems has long favored them as ligands in metal catalysis. The last decade saw pyridine assume a stronger role as functional group for directed C–H oxidation/activation.Reference of Pyridin-3-ylboronic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of C6H4BrNOIn 2017 ,《Silver-Catalysed Domino Approach to 1,3-Dicarbo-Substituted Isochromenes》 was published in European Journal of Organic Chemistry. The article was written by Dell’Acqua, Monica; Pirovano, Valentina; Peroni, Stefano; Tseberlidis, Giorgio; Nava, Donatella; Rossi, Elisabetta; Abbiati, Giorgio. The article contains the following contents:

Authors report herein the first example of the silver triflate catalyzed synthesis of 1,3-dicarbo-substituted isochromene derivatives starting from 2-alkynyl(hetero)arylaldehydes and enolizable ketones. The reaction proceeds in a cascade fashion under mild heating with complete regioselectivity and moderate-to-good yields. In some cases, the reaction gives unexpected homodimeric products. Two competitive mechanistic paths for the formation of the desired isochromene derivatives and the homodimeric products are described. In addition to this study using 2-Bromonicotinaldehyde, there are many other studies that have used 2-Bromonicotinaldehyde(cas: 128071-75-0Synthetic Route of C6H4BrNO) was used in this study.

2-Bromonicotinaldehyde(cas: 128071-75-0) 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. Synthetic Route of C6H4BrNO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Formula: C7H6BrNO2In 2019 ,《Design, biological evaluation and X-ray crystallography of nanomolar multifunctional ligands targeting simultaneously acetylcholinesterase and glycogen synthase kinase-3》 was published in European Journal of Medicinal Chemistry. The article was written by Oukoloff, Killian; Coquelle, Nicolas; Bartolini, Manuela; Naldi, Marina; Le Guevel, Remy; Bach, Stephane; Josselin, Beatrice; Ruchaud, Sandrine; Catto, Marco; Pisani, Leonardo; Denora, Nunzio; Iacobazzi, Rosa Maria; Silman, Israel; Sussman, Joel L.; Buron, Frederic; Colletier, Jacques-Philippe; Jean, Ludovic; Routier, Sylvain; Renard, Pierre-Yves. The article contains the following contents:

Two scaffolds, targeting AChE (tacrine) and GSK-3α/β (valmerin) simultaneously, were assembled, using copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), to generate a new series of multifunctional ligands. A series of eight multi-target directed ligands (MTDLs) was synthesized and evaluated in-vitro and in cell cultures. Mol. docking studies, together with the crystal structures of three MTDL/TcAChE complexes, with three tacrine-valmerin hybrids allowed designing an appropriate linker containing a 1,2,3-triazole moiety whose incorporation preserved and even increased, the original inhibitory potencies of the two selected pharmacophores toward the two targets. Most of the new derivatives exhibited nanomolar affinity for both targets and the most potent compound of the series displayed inhibitory potencies of 9.5 nM for human acetylcholinesterase (hAChE) and 7 nM for GSK-3α/β. These novel dual MTDLs was served as suitable leads for further development, since, in the micromolar range, they exhibited low cytotoxicity on a panel of representative human cell lines including the human neuroblastoma cell line SH-SY5Y. Moreover, these tacrine-valmerin hybrids displayed a good ability to penetrate the blood-brain barrier (BBB) without interacting with efflux pumps such as P-gp. In the experimental materials used by the author, we found Methyl 5-bromopicolinate(cas: 29682-15-3Formula: C7H6BrNO2)

Methyl 5-bromopicolinate(cas: 29682-15-3) 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. Formula: C7H6BrNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem