13131-02-7

Usage

Uses

Used in Pharmaceutical Industry:
N-PHENYLPYRIDIN-2(1H)-ONE is used as a metabolite of Pirfenidone for the treatment of patients with kidney disease who have diabetes. Its presence in the drug helps in managing the condition and improving the overall health of the patients.

Upstream product

• 4783-68-0 2-phenoxypyridine 
• 857216-93-4 2,2-dichloro-1-phenyl-1,2-dihydro-pyridine 
• 142-08-5 2-Pyridone 
• 462-80-6 benzyne 
• 142-08-5 2-hydroxypyridin 
• 108-86-1 bromobenzene 
• 103-71-9 phenyl isocyanate 
• 74-86-2 acetylene 
• 118-92-3 anthranilic acid 
• 603-33-8 triphenylbismuthane 
• 934-56-5 trimethyl(phenyl)stannane 
• 23353-96-0 pyridin-2(3H)-one 
• 4789-09-7 1-phenylpiperidin-2-one 
• 591-50-4 iodobenzene 

Downstream Products

• 857216-93-4 2,2-dichloro-1-phenyl-1,2-dihydro-pyridine 
• 99866-60-1 3,5-dichloro-1-phenyl-2-pyridone 
• 120491-70-5 3-bromo-1-phenyl-2-pyridone 
• 120491-71-6 3,5-dibromo-1-phenylpyridin-2(1H)-one 
• 120491-72-7 3,5-diiodo-1-phenyl-2-pyridone 
• 120491-73-8 3,5-dinitro-1-phenyl-2-pyridone 
• 126957-56-0 1-phenyl-1H-pyridine-2-thione 
• 1186308-09-7 C₁₄H₁₅NO 
• 1186307-86-7 C₁₄H₁₅NO 

Relevant academic research and scientific papers

PhICl2/NH4SCN-Mediated Oxidative Regioselective Thiocyanation of Pyridin-2(1H)-ones

The reaction of pyridin-2(1H)-ones with PhICl2 and NH4SCN enables an efficient regioselective thiocyanation, leading to the synthesis of the biologically interesting C5 thiocyanated 2-pyridones in good to high yields. The mechanistic pathway of this metal-free approach is postulated to involve the formation of the reactive thiocyanogen chloride from the reaction of PhICl2 and NH4SCN followed with the regioselective electrophilic thiocyanation of the pyridin-2(1H)-one ring.

C-H Pyridonation of (Hetero-)Arenes by Pyridinium Radical Cations

Pyridones are important heteroaromatic scaffolds found in natural products and pharmaceuticals and are, therefore, of major interest in organic synthetic chemistry. Here we report the first C-H pyridonation of unactivated (hetero-)arenes, providing a methodology to directly access N-aryl-2- and 4-pyridones. Generation of pyridinium radical cations through single-electron reduction allows for the synthesis of pyridones on structurally complex molecules.

Structure Ligation Relationship of Amino Acids for the Amination Cross-Coupling Reactions

The structure ligation relationship (SLR) of amino acids (AAs) for the cross-coupling aminations was examined. While AA ligated C-N cross-couplings under Pd and Ni catalysis were minor or ineffective, the AA ligated Cu-catalyzed C-N cross-couplings were promising particularly with the use of l-methionine. The roles of -NH2, -CO2H, and -S- of l-methionine were investigated and found critical for their ligation efficiency. The finding was compatible with aromatic as well as aliphatic amines including tautomerizable N-heteroarenes.

Synthesis of N-aryl pyridin-2-ones via ligand coupling reactions using pentavalent organobismuth reagents

An efficient method for the synthesis of N-aryl pyridin-2-ones was established by way of ligand coupling reactions using pentavalent organobismuth reagents such as triarylbismuth dichlorides. Copyright

An unusual rearrangement involving 5-bromo-1-phenylpyridone during its methyl cross coupling with turbo-Grignard reagent, leading to a 5-bromopyridone-fused seven-membered carbocyclic ring

[Figure not available: see fulltext.] The structure of a cyclohepta[c]pyridin-1-one, a product of an unusual transformation, isolated during a turbo-Grignard reagentpromoted methyl cross coupling to 5-bromo-1-phenyl-2-pyridone, was determined by 1H and 13C NMR, COSY and high-resolution MS, as well as computer modeling. Its formation suggests a remarkable nucleophilic attack at the α-position to the pyridone carbonyl group. A rational pathway is presented.

Activated charcoal supported copper nanoparticles: A readily available and inexpensive heterogeneous catalyst for the N-arylation of primary amides and lactams with aryl iodides

A novel heterogeneous copper catalyst has been developed by supporting copper nanoparticles on activated charcoal via in situ reducing copper(II) with aqueous hydrazine as reductant. The characterization of Cu/C catalyst showed that the Cu0 nano-particles were formed on the surface of charcoal. This catalyst displayed good catalytic activities toward the N-arylation of primary amides and lactams with aryl iodides.

Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis

The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.

Manganese-Promoted Regioselective Direct C3-Phosphinoylation of 2-Pyridones

A highly efficient and regioselective manganese-induced radical oxidative direct C?P bond formation between 2-pyridones and secondary phosphine oxides was developed. The C3-selective phosphinoylation was conveniently achieved through a combination of substoichiometric manganese and persulfate oxidant under mild conditions. Various 3-phosphinoylated pyridone products can be obtained in moderate to high yields. Preliminary mechanistic studies suggest that the reaction is likely to involve a radical pathway induced by catalytically active Mn3+ species.

Light-induced [2 + 2] cycloadditions for the construction of cyclobutane-fused pyridinyl sulfonyl fluorides

Cyclobutanes are an important class of motifs present in a wide range of natural products and other biologically significant molecules. A photocatalytic [2 + 2] cycloaddition between pyridones or isoquinolones and ethenesulfonyl fluoride was achieved, providing a portal to a class of unique cyclobutane-fused pyridinyl sulfonyl fluorides with quaternary rigid rings (30 examples). Further applications of these novel sulfonyl fluoride molecules in SuFEx click chemistry were also accomplished, providing the corresponding sulfonates and sulphonamides with reasonable yields.

N - And O -arylation of pyridin-2-ones with diaryliodonium salts: Base-dependent orthogonal selectivity under metal-free conditions

Metal-free N- and O-arylation reactions of pyridin-2-ones as ambident nucleophiles have been achieved with diaryliodonium salts on the basis of base-dependent chemoselectivity. In the presence of N,N-diethylaniline in fluorobenzene, pyridin-2-ones were very selectively converted to N-arylated products in high yields. On the other hand, the O-arylation reactions smoothly proceeded with the use of quinoline in chlorobenzene, leading to high yields and selectivities. In these methods, a variety of pyridin-2-ones in addition to pyridin-4-one and a set of diaryliodonium salts were accepted as suitable reaction partners.