25160-82-1

Upstream product

• 2048-37-5 1-methyl-3-phenylquinoxalin-2(1H)-one (3a) 
• 611-73-4 Benzoylformic acid 
• 6479-18-1 1-methyl-2(1H)-quinoxalinone 
• 98-80-6 phenylboronic acid 
• 780-69-8 triethoxyphenylsilane 
• 25148-68-9 N-methylbenzene-1,2-diamine dihydrochloride 
• 1504-78-5 3-phenylquinoxaline-2(1H)-one 

Downstream Products

• 2048-37-5 1-methyl-3-phenylquinoxalin-2(1H)-one (3a) 

Relevant academic research and scientific papers

Palladium-catalyzed direct Hiyama arylation of quinoxalin-2(1H)-ones with aryl siloxanes in water

An efficient method for palladium-catalyzed direct Hiyama coupling of various quinoxalin-2(1H)-ones with aryl siloxanes has been developed. The protocol provides a convenient access to a variety of useful C3-arylated 1-methylquinoxalin-2(1H)-one derivatives in reasonable yields by using low cost water as a solvent and oxygen as an oxidant.

Renewable Molecular Flasks with NADH Models: Combination of Light-Driven Proton Reduction and Biomimetic Hydrogenation of Benzoxazinones

Using small molecules with defined pockets to catalyze chemical transformations resulted in attractive catalytic syntheses that echo the remarkable properties of enzymes. By modulating the active site of a nicotinamide adenine dinucleotide (NADH) model in a redox-active molecular flask, we combined biomimetic hydrogenation with in situ regeneration of the active site in a one-pot transformation using light as a clean energy source. This molecular flask facilitates the encapsulation of benzoxazinones for biomimetic hydrogenation of the substrates within the inner space of the flask using the active sites of the NADH models. The redox-active metal centers provide an active hydrogen source by light-driven proton reduction outside the pocket, allowing the in situ regeneration of the NADH models under irradiation. This new synthetic platform, which offers control over the location of the redox events, provides a regenerating system that exhibits high selectivity and efficiency and is extendable to benzoxazinone and quinoxalinone systems.

Assisted tandem palladium(II)/palladium(0)-catalyzed C-and N-Arylations of quinoxalin-2(1H)-ones in water

A straightforward assisted tandem palladium(II)-and palladium(0)-catalyzed direct C-3 and N-4 arylation of quinoxalin-2(1H)-ones with boronic acids and aryl halides in water as safe and cheap solvent is reported. This environmentally friendly catalytic protocol is compatible with a wide range of functional groups and allows construction of various biologically important quinoxalin-2(1H)-one backbones.

Palladium(II)-catalyzed oxidative arylation of quinoxalin-2(1 H)-ones with arylboronic acids

A straightforward palladium-catalyzed oxidative C-3 arylation of quinoxalin-2(1H)-ones with arylboronic acids is reported. This protocol is compatible with a wide range of functional groups and allows construction of various biologically important quinoxalin-2(1H)-one backbones.

The first general, highly enantioselective lewis base organocatalyzed hydrosilylation of benzoxazinones and quinoxalinones

The first general, highly enantioselective hydrosilylation of benzoxazinones and quinoxalinones has been developed. The chiral Lewis base organocatalysis that are readily accessible from (1S,2R)-ephedrine and (1R,2S)-ephedrine promoted the title reaction to afford various chiral dihydrobenzoxazinones and dihydroquinoxalinones with good yields as well as good enantioselectivities.

Formal hydride transfer mechanism for photoreduction of 3-phenylquinoxalin-2-ones by amines. Association of 3-phenylquinoxalin-2-one with aliphatic amines

The photophysical and photochemical behavior of 1-methyl-3-phenylquinoxalin-2-one (MeNQ) and 3-phenylquinoxalin-2-one (HNQ) in the presence of amines is reported. While HNQ fluorescence shows an auxochromic effect and a bathochromic shift with added amine

Photochemical Reactions of Quinoxalin-2-ones and Related Compounds

Irradiation of the quinoxalin-2-ones (1a-c, e-g and i) in the presence of amines gave reductive dimers, the dihydro dimers (3a-c, e-g and i) of quinoxalin-2-ones, while irradiation of the quinoxalin-2-ones (1d, h and j), which possess a phenyl group at th

Photochemical Reductive Dimerization of Quinoxalin-2-ones and 1,4-Benzoxazin-2-one

Irradiation of the quinoxalin-2-ones (1a-d) in the presence of amine gave the quinoxalin-2-one reductive dimers (2a-d), while irradiation of the 1,4-benzoxazin-2-one (4) under similar conditions gave two stereoisomeric reductive dimers .