19006-80-5

Upstream product

• 142-08-5 2-hydroxypyridin 
• 624-31-7 4-tolyl iodide 
• 142-08-5 2-Pyridone 
• 5720-05-8 4-methylphenylboronic acid 
• 106-38-7 para-bromotoluene 
• 106-43-4 para-chlorotoluene 
• 23353-96-0 pyridin-2(3H)-one 

Relevant academic research and scientific papers

An efficient copper-catalyzed coupling reaction of pyridin-2-ones with aryl and heterocyclic halides based on Buchwald's protocol

An efficient copper-catalyzed coupling reaction based on the Buchwald's protocol has been established for pyridin-2-ones with aryl iodides, aryl bromides, and heterocyclic bromides.

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.

Substituent Effects of 2-Pyridones on Selective O-Arylation with Diaryliodonium Salts: Synthesis of 2-Aryloxypyridines under Transition-Metal-Free Conditions

An efficient transition-metal-free strategy to synthesize 2-aryloxypyridine derivatives has been developed by a selective O-arylation of 2-pyridones with diaryliodonium salts. The reaction was compatible with a series of functional groups for 2-pyridones and diaryliodonium salts such as halides, nitro, cyano, and ester groups. The substituents at the C6-position of 2-pyridones favored O-arylation products because of steric hindrance. The reaction was easily performed on a gram-scale and 6-chloro-2-pyridone was a good precursor to access various unsubstituted 2-aryloxypyridines by dehalogenation. A P2Y 1 lead compound analogue could be prepared in good yield over two steps.

Copper-Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amides

Cu2O/N,N′-bis(thiophen-2-ylmethyl)oxalamide is established to be an effective catalyst system for Goldberg amidation with inferior reactive (hetero)aryl chlorides, which have not been efficiently documented by Cu-catalysis to date. The reaction is well liberalized toward a variety of functionalized (hetero)aryl chlorides and a wide range of aromatic and aliphatic primary amides in good to excellent yields. Furthermore, the arylation of lactams and oxazolidinones is achieved. The present catalytic system also accomplished an intramolecular cross-coupling product.

N-arylation of pyridin-2(1H)-ones with pentavalent organobismuth reagents under copper-free conditions

An efficient method for the N-arylation of pyridin-2(1H)-ones and the related heteroaromatic lactams has been established via ligand-coupling reactions using tri- or tetra-aryl organobismuth(V) reagents such as triarylbismuth dichlorides. Also, N-alkenylation of pyridin-2(1H)-one was achieved similarly by using alkenyltriarylbismuth(V) reagents.

Copper-catalyzed general C-N and C-O bond cross-coupling with arylboronic acid

General catalytic Cu(OAc)2/TEMPO in air or Cu(OAc)2/O2 systems for the C-N and C-O cross-coupling reactions with arylboronic acid have been discovered. N- and O-vinylation have also been demonstrated.

Copper promoted aryl/saturated heterocyclic C-N bond cross-coupling with arylboronic acid and arylstannane

Arylboronic acid/cupric acetate arylation of N-H containing saturated heterocycles has been explored and found to give good yields of the cross- coupled products. Phenyltrimethylstannane is also found to arylate N-H containing heterocycles.

N-aryl heterocycles via coupling reactions with arylboronic acids

Compounds having a partial 2-pyridone structure or 3-pyridazinones can be selectively N-arylated with phenylboronic acids according to the procedure described by Chan and Lam. This procedure leads to N5-arylated imidazo[4,5- c]pyridin-4-ones, precursors of potent factor Xa inhibitors. In addition, the synthesis of N-aryl substituted pyrrole- and indole-2-carboxylic acid esters is described. In the indole series this procedure offers a flexible entry in the synthesis of different 1,3-diaryl-2-carboxyindoles.

A facile copper-catalyzed Ullmann condensation: N-arylation of heterocyclic compounds containing an -NHCO- moiety

N-Aryl heterocyclic compounds were synthesized from aryl halides and heterocyclic compounds containing an -NHCO- moiety by using a catalytic amount (1-10 mol%) of a commercially available copper catalyst in satisfactory yields. This catalytic reaction was applicable to the synthesis of N-aryl-2-pyridone, -2-pyrrolidone, -1(2H)-isoquinolone, -1(2H)- phthalazinone, -4(3H)-quinazolinone and -1,2,3-benzotriazin-4(3H)-one derivatives.