60544-07-2

Upstream product

• 30100-35-7 p-anisyl-p-benzoquinone 
• 106-99-0 buta-1,3-diene 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 104-94-9 4-methoxy-aniline 
• 198348-19-5 2-Chlor-3-(4-methoxyphenyl)-1,4-naphthochinon 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 130-15-4 [1,4]naphthoquinone 
• 90-15-3 α-naphthol 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 115298-63-0 phenyl(4-methoxyphenyl)iodonium triflate 
• 141339-54-0 bis(4-anisyl)iodonium triflate 
• 100-66-3 methoxybenzene 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 

Downstream Products

• 107522-68-9 1,4-dihydroxy-3-(4-methoxy-phenyl)-[2]naphthonitrile 
• 79060-47-2 1,7a-Bis-(4-methoxy-phenyl)-1a,7a-dihydro-1H-1-aza-cyclopropa[b]naphthalene-2,7-dione 
• 79060-41-6 2-(4-Methoxy-phenyl)-3-(4-methoxy-phenylamino)-[1,4]naphthoquinone 
• 79060-35-8 2-(4-Methoxy-phenyl)-2-{[(Z)-4-methoxy-phenylimino]-methyl}-indan-1,3-dione 
• 92796-03-7 (4-hydroxyphenyl)naphthalene-1,4-dione 
• 1380443-78-6 2-(4-methoxyphenyl)-3-(pyrrolidin-1-yl)naphthalene-1,4-dione 
• 1134320-10-7 N-[3-(4-methoxyphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]benzamide 
• 107523-20-6 3-(4-methoxy-phenyl)-1,4-dioxo-1,4-dihydro-[2]naphthonitrile 
• 1445849-81-9 2-(4-methoxyphenyl)-3-(trifluoromethyl)naphthalene-1,4-dione 

Relevant academic research and scientific papers

The silver catalyzed direct C-H functionalization of quinones with dialkyl amides

DMA and other dialkylamides were successfully used as synthons for the C-H functionalization of quinones. This novel amidoalkylation reaction works with a variety of substituted quinones and dialkyl/alkyl amides, such as DMF, NMP and NMA, and the corresponding products were obtained in moderate to good yields. The amidoalkylation of quinones is demonstrated for the first time. A suitable mechanism and the synthetic utility of these compounds are demonstrated. The molecular docking of compound 5 with an Alzheimer's disease (AD) associated AChE target site was studied.

Ruthenium(II)- and Palladium(II)-catalyzed position-divergent C–H oxygenations of arylated quinones: Identification of hydroxylated quinonoid compounds with potent trypanocidal activity

A diversity-oriented synthesis of hydroxylated aryl-quinones via C–H oxygenation reactions and their evaluation against Trypanosoma cruzi, the etiological agent of Chagas disease, was accomplished. With the use of ruthenium(II)- or palladium(II)-based cat

Approach to the Synthesis of Unsymmetrical/Symmetrical Maleimides via Desulfitative Arylation at Different Temperatures

New routes toward selective synthesis of both mono-and diaryl maleimides have been innovated. The mere requirement to this end is through the increase of temperature. The method works effectively for maleic anhydride and maleic acid as well. Also, the fir

Palladium-catalyzed arylation of 1,4-naphthoquinones with aryl iodides and its synthetic application to the benzo[b]phenanthridine skeleton

We report a Pd-catalyzed arylation of 1,4-naphthoquinones with aryl iodides. This reaction shows excellent functional group tolerance and high regioselectivity when using nonsymmetric 1,4-naphthoquinone. Furthermore, the resulting 2-aryl-1,4-naphthoquinon

CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones: Efficient synthesis of 1,4-naphthoquinones

A concise and efficient method for the synthesis of 1,4-naphthoquinones has been successfully developed involving a CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones. The present protocol provided a novel approach to access functionalized 1,4-naphthoquinones from non-naphthoquinone precursors with good selectivity and functional group tolerance.

NHC-Catalyzed Dual Stetter Reaction: A Mild Cascade Annulation for the Syntheses of Naphthoquinones, Isoflavanones, and Sugar-Based Chiral Analogues

The N-heterocycle carbene (NHC)-catalyzed dual Stetter cascade reaction is discovered through coupling of β-nitrostyrene with phthalaldehyde under mild conditions to furnish valuable aryl-naphthoquinones. The generality of the new reaction is validated through the development of a C-C and O-C bond forming Stetter cascade reaction using salicylaldehydes to obtain functionalized dihydroisoflavanones. The mild NHC organocatalysis is successfully employed for the construction of optically pure sugar-based naphthoquinones and dihydroisoflavanones. Herein, NHC is found as a unique and powerful organocatalyst to construct homoatomic C-C cross-coupling, heteroatomic O-C bond formation, and cascade cyclization utilizing NO2 as a leaving group at ambient temperature. A mechanistic pathway of the new metal-free catalysis is predicted on the basis of our ESI-MS study of the ongoing reaction and literature.

Comprehensive evaluation of antioxidant effects of Japanese Kampo medicines led to identification of Tsudosan formulation as a potent antioxidant agent

Oxidative stress due to the overproduction of reactive oxygen species plays an important role in the pathogenesis of various diseases. In the present study, we comprehensively evaluated the antioxidant activities of 147 oral formulations of Japanese traditional herbal medicines (Kampo medicines), representing the entire panel of oral Kampo medicines listed in the Japanese National Health Insurance Drug List, using in vitro radical scavenging assays, including the 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity assay, the superoxide anion scavenging activity assay, and the oxygen radical absorption capacity assay. Three of the formulations tested, namely, Tsudosan, Daisaikoto, and Masiningan, showed the most potent in vitro antioxidant activities and were selected for further investigation of their intracellular and in vivo antioxidant effects. The results of the 2′,7′-dichlorodihydrofluorescin diacetate assay demonstrated that all three Kampo medicines significantly inhibited hydrogen peroxide-induced oxidative stress in human hepatocellular liver carcinoma HepG2 cells. In addition, Tsudosan significantly increased the serum biological antioxidant potential values when orally administrated to mice, indicating that it also had in vivo antioxidant activity. The potent antioxidant activity of Tsudosan may be one of the mechanisms closely correlated to its clinical usage against blood stasis.

Nonaqueous arylated quinone catholytes for lithium-organic flow batteries

Chemically modified organic redox couples have the advantages of tunable redox properties, high solubility, environmental benignity, and cost effectiveness. Inspired by nature, a series of quinone derivatives bearing electron-donating methoxy or electron-withdrawing trifluoromethyl groups are synthesized in moderate to high yields by Pd-catalyzed Suzuki cross-coupling reactions. This study utilizes the synthetic quinones as redox-active organic molecules for nonaqueous lithium-organic flow batteries. The aryl moiety incorporated quinone scaffolds show enhanced electrochemical stability and rate capability. The nonaqueous catholyte, 2-phenyl-1,4-naphthoquinone, reaches a cell voltage of ～2.6 V and a specific capacity of 196 mA h g-1, while the discharge capacity is retained at ～92% for 150 cycles. Moreover, the tubular lithium-organic flow battery system features stable cycle performance under a continuous circulation without clogging-associated intermittency flow.

Method for synthesizing 2-substituted-1,4-naphthoquinone compound

The invention discloses a method for synthesizing a 2-substituted-1,4-naphthoquinone compound. The method comprises the following steps: by taking a 2-alkynyl acetophenone compound of a formula I as shown in the specification as a raw material, in the presence of a copper catalyst, by taking Selectfluor as an oxidant, adding an alkali substance, performing a stirring reaction for 10-24 hours at 70 DEG C in a mixed solvent of acetonitrile and water, and after the reaction is completed, and performing aftertreatment on reaction liquid, thereby obtaining the 2-substituted-1,4-naphthoquinone compound of a formula II as shown in the specification. By adopting the method disclosed by the invention, the raw materials are variable, a great amount of derivatives can be generated, the catalyst is cheap and easy to obtain, the cost can be greatly lowered, and no pollution can be caused; oxygen sources used in the method are water and Selectfluor; the reaction condition is gentle, and energy consumption can be reduced; in addition, the method has the characteristics of being high in yield, good in substrate universality, simple and convenient in aftertreatment operation, and the like.

Hauser–Kraus Annulation of Phthalides with Nitroalkenes for the Synthesis of Fused and Spiro Heterocycles

Hauser–Kraus annulation of sulfonylphthalides with simple conjugated nitroalkenes follows the expected pathway to furnish naphthoquinones in moderate yields. However, a strategic variation of this reaction by employing nitroalkenes bearing an additional nucleophilic site results in [4+4] annulation leading to complex fused and spiro heterocycles in high yields with high selectivity through a cascade process involving Michael addition, Dieckmann cyclization, and a series of eliminations and rearrangements.