Category: 39856-58-1

Maust, Mark C. published the artcileSwitchable Regioselective 6-endo or 5-exo Radical Cyclization via Photoredox Catalysis, SDS of cas: 39856-58-1, the publication is Journal of the American Chemical Society (2022), 144(9), 3776-3781, database is CAplus and MEDLINE.

Here a simple method for reagent controlled regioselective radical cyclization of halogenated N-heterocycles onto pendant olefins was developed. Radical generation occurs under mild photoredox conditions with control of the regioselectivity governed by the rate of hydrogen atom transfer (HAT). Utilizing a polarity-matched thiol-based HAT agent promoted the highly selective formation of the 5-exo cyclization product. Conversely, limiting the solubility of the HAT reagent Hantzsch ester (HEH) leads to selective formation of the thermodynamically favored 6-endo product. This occurs through an initial 5-exo cyclization, with the resulting alkyl radical intermediate undergoing neophyl rearrangement to form the 6-endo product. Development of this switchable catalysis strategy allows for two modes of divergent reactivity to form either the 6-endo or 5-exo product, generating fused N-heteroaromatic/saturated ring systems.

Journal of the American Chemical Society published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, SDS of cas: 39856-58-1.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Qu, Bo published the artcileChelation controlled reductive amination of cyclic ketones to trans-4-methoxycyclohexylamines: 9-BBN reduction mediated with FeCl₃, Application of 2-Bromopyridin-3-amine, the publication is Tetrahedron Letters (2012), 53(15), 1982-1986, database is CAplus.

A novel trans-diastereoselective reductive amination of 4-substituted cyclohexanones is described using 9-BBN as reducing agent in the presence of FeCl₃. The method permits efficient synthesis of structurally diverse 4-trans-alkoxycyclohexylamines.

Tetrahedron Letters published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Application of 2-Bromopyridin-3-amine.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Lawson, Marie published the artcileAn efficient coupling of N-tosylhydrazones with 2-halopyridines: synthesis of 2-α-styrylpyridines endowed with antitumor activity, SDS of cas: 39856-58-1, the publication is Organic & Biomolecular Chemistry (2013), 11(22), 3664-3673, database is CAplus and MEDLINE.

The synthesis of 2-α-styrylpyridines has been carried out by using the coupling of polyoxygenated N-tosylhydrazones with various 2-halopyridines. We demonstrated that the use of a catalytic amount of PdCl₂(MeCN)₂ in combination with a bidentate ferrocene DPPF or a monodentate alkyl phosphine ^tBu₂MeP-HBF₄ constitutes an efficient protocol for this coupling, providing 2-α-styrylpyridines in satisfactory to good yields. Among evaluated, compound I was found to exhibit excellent antiproliferative and antimitotic activities comparable to that of the reference compound isoCA-4.

Organic & Biomolecular Chemistry published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, SDS of cas: 39856-58-1.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Blanchard, Stephanie published the artcileDihydrodipyridopyrazines: synthesis and functionalization, Safety of 2-Bromopyridin-3-amine, the publication is Studii si Cercetari Stiintifice: Chimie si Inginerie Chimica, Biotehnologii, Industrie Alimentara (Universitatea Bacau) (2010), 11(1), 45-65, database is CAplus.

This paper is a combination of the authors’ prior published work with new exptl. material. Different conceptual synthetic approaches to the elaboration of a new family of planar polynuclear nitrogen containing aromatic heterocycles – the dihydrodipyridopyrazines – are reviewed: the arynic reaction, the sequence palladium coupling reaction – substitution – reduction – cyclization – substitution or via Smiles rearrangement. Further functionalization of these compounds by substitution reaction, metalation sequence and palladium-catalyzed coupling reaction are also discussed.

Studii si Cercetari Stiintifice: Chimie si Inginerie Chimica, Biotehnologii, Industrie Alimentara (Universitatea Bacau) published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Safety of 2-Bromopyridin-3-amine.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Li, Zhao published the artcilePd-Catalyzed Suzuki coupling reactions of aryl halides containing basic nitrogen centers with arylboronic acids in water in the absence of added base, Category: pyridine-derivatives, the publication is New Journal of Chemistry (2017), 41(24), 15420-15432, database is CAplus.

The Pd-catalyzed Suzuki coupling reactions of a series of aryl chlorides and aryl bromides containing basic nitrogen centers with arylboronic acids in water in the absence of added base were reported. The reactions proceeded either partially or entirely under acidic conditions. After surveying twenty-two phosphorus ligands, high yields of products were obtained with aryl chlorides only when a bulky ligand, 2-(di-tert-butyl-phosphino)-1-phenyl-1H-pyrrole (cataCXiumPtB) was used. In contrast, aryl bromides produced high yields of products in the absence of both added base and added ligand. In order to explore the Suzuki coupling process entirely under acidic conditions, a series of reactions were conducted in buffered acidic media using several model substrates. 4-Chlorobenzylamine, in the presence of cataCXiumPtB, produced high yields of product at buffered pH 6.0; the yields dropped off precipitously at buffered pH 5.0 and lower. The fall-off in yield was attributed to the decomposition of the Pd-ligand complex due to the protonation of the ligand in the more acidic aqueous media. In contrast, in the absence of an added ligand, 4-amino-2-chloropyridine produced quant. yields at buffered pH 3.5 and 4.5 while 4-amino-2-bromopyridine produced quant. yields in a series of buffered media ranging from pH 4.5 to 1.5. These substrates were only partially protonated in acidic media and could behave as active Pd ligands in the Suzuki catalytic cycle.

New Journal of Chemistry published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Category: pyridine-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Li, Zhao published the artcileAqueous Suzuki Coupling Reactions of Basic Nitrogen-Containing Substrates in the Absence of Added Base and Ligand: Observation of High Yields under Acidic Conditions, Product Details of C5H5BrN2, the publication is Journal of Organic Chemistry (2016), 81(18), 8520-8529, database is CAplus and MEDLINE.

A series of aqueous heterogeneous Suzuki coupling reactions of substrates containing basic nitrogen centers with phenylboronic acid in the absence of added base and ligand is presented. High yields of products were obtained by employing aryl bromides containing aliphatic 1°, 2°, and 3° amine substituents, and good to high yields were obtained by employing a variety of substituted bromopyridines. In the former series, the pH of the aqueous phase changed from basic to acidic during the course of the reaction, while in the latter series the aqueous phase was on the acidic side of the pH scale throughout the entire course of reaction. A mechanistic interpretation for these observations, which generally preserves the oxo palladium catalytic cycle widely accepted in the literature, is presented.

Journal of Organic Chemistry published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Product Details of C5H5BrN2.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Perez-Gomez, Marta published the artcileTrapping σ-Alkyl-Palladium(II) Intermediates with Arynes Encompassing Intramolecular C-H Activation: Spirobiaryls through Pd-Catalyzed Cascade Reactions, Formula: C5H5BrN2, the publication is Angewandte Chemie, International Edition (2016), 55(46), 14389-14393, database is CAplus and MEDLINE.

A palladium-catalyzed cascade reaction based on the trapping of transient alkyl-Pd^II intermediates with arynes encompassing a C-H activation step has been developed. This synthetic pathway gives rise to hetero-spirocyclic scaffolds containing a biaryl motif, and opens up new synthetic strategies in the design of cascade reactions since it gathers several aspects of Pd chem., i.e., intra- and intermol. carbopalladation of unsaturated species, C-H activation and C-C coupling processes.

Angewandte Chemie, International Edition published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Formula: C5H5BrN2.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Sadig, Jessie E. R. published the artcilePalladium-Catalyzed Synthesis of Benzimidazoles and Quinazolinones from Common Precursors, Category: pyridine-derivatives, the publication is Journal of Organic Chemistry (2012), 77(21), 9473-9486, database is CAplus and MEDLINE.

N-(o-Halophenyl)imidoyl chlorides and the corresponding imidates are easily prepared and can be utilized as complementary precursors for the synthesis of important heterocycles. The synthesis of N-substituted benzimidazoles was possible from the palladium-catalyzed reaction of both classes of substrate with a variety of N-nucleophiles. The use of the imidate precursor for the synthesis of N-substituted quinazolinones by incorporation of a palladium-catalyzed aminocarbonylation reaction has also been demonstrated. Both processes tolerate a wide range of functional groups.

Journal of Organic Chemistry published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Category: pyridine-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Raydan, Daniel published the artcileManganese-Catalyzed Synthesis of Imines from Primary Alcohols and (Hetero)Aromatic Amines, COA of Formula: C5H5BrN2, the publication is Synlett (2022), 33(13), 1290-1294, database is CAplus.

Herein, the synthesis of a wide variety of imines through oxidative coupling of alcs. and aromatic amines catalyzed by Mn complexes bearing NN triazole ligands was described. A wide variety of imines in excellent yields (up to 99%) was prepared Mn-based catalysts proved to be highly efficient and versatile, allowing for the first time the preparation of several imines containing N-based heterocycles.

Synlett published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, COA of Formula: C5H5BrN2.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Wang, Kun published the artcileTetraphosphine/palladium-catalyzed Suzuki-Miyaura coupling of heteroaryl halides with 3-pyridine- and 3-thiopheneboronic acid. An efficient catalyst for the formation of biheteroaryls, Safety of 2-Bromopyridin-3-amine, the publication is Applied Organometallic Chemistry (2013), 27(4), 232-238, database is CAplus.

An easily prepared tetraphosphine N,N,N’,N’-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine associated with [Pd(η³-C₃H₅)Cl]₂ affords an efficient catalyst for Suzuki-Miyaura coupling of 3-pyridineboronic acid with heteroaryl bromides. Reaction could be performed with as little as 0.02 mol% catalyst and a high turnover number of 2500 is obtained. A wide range of substrates is investigated with satisfactory yields, and good compatibility with aminogroup-substituted pyridines and unprotected indole is exhibited. This protocol can also be applied successfully to the reaction of heteroaryl bromides with 3-thiopheneboronic acid. This Pd-tetraphosphine catalyst efficiently restrains the poisoning effect from heteroaryls, and shows good stability and longevity.

Applied Organometallic Chemistry published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C12H21NO7, Safety of 2-Bromopyridin-3-amine.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem