329015-19-2

Upstream product

• 95-20-5 2-methyl-1H-indole 
• 615-93-0 2,5-Dichloro-1,4-benzoquinone 

Relevant academic research and scientific papers

Organometallic routes to 2,5-dihydroxy-3-(indol-3-yl)benzoquinones. Synthesis of demethylasterriquinone B4

(Figure Presented) A method has been developed to sequentially add indole-3-mercurials to dichlorinated quinones using palladium catalysis. These reactions can be used in the modular assembly of bis(indol-3-yl)-benzoquinones, a significant natural product family.

Hypoiodite-catalysed oxidative homocoupling of arenols and tandem oxidation/cross-coupling of hydroquinones with arenes

We report the hypoiodite-catalyzed oxidative C-C homocoupling of arenols to biarenols or biquinones using aqueous hydrogen peroxide as an oxidant. In addition, by combining hypoiodite catalysis and lipophilic Lewis acid-assisted Br?nsted acid catalysis under aqueous conditions, we achieved a tandem oxidation/cross-coupling reaction of hydroquinones with electron-rich arenes. These results highlight the substantial scope of hypoiodite/acid co-catalysis for use in oxidative coupling reactions.

METHOD FOR PRODUCING ARYLHYDROQUINONES AND METHOD FOR PRODUCING ARYLQUINONES

PROBLEM TO BE SOLVED: To produce arylhydroquinones and arylquinones in mild conditions without using a rare metal catalyst. SOLUTION: A method for producing arylhydroquinones by Michael addition of a an aryl compound with quinones in the presence of a catalyst. As the catalyst, the combination of a Lewis acid and a Bronsted acid is used. As the Lewis acid, M(BAr4)n (M is an alkali metal, an alkali earth metal or a triarylmethyl; four Ar's are aryl having an electron-withdrawing group and four Ar's may be the same or different; and n is the same number as the valence of M) is used. For example, an aimed product is produced by Michael addition of 1,3-dimethoxybenzene with 1,2-benzoquinone in the presence of a catalytic amount of Li[B(C6F5)4] and an oxalic acid. COPYRIGHT: (C)2015,JPOandINPIT

"On water"-promoted direct coupling of indoles with 1,4-benzoquinones without catalyst

A highly efficient direct coupling of indole compounds with 1,4-benzoquinones was developed "on water" in the absence of any catalyst, organic co-solvent, or additives. The "on-water" conditions provided the best yields of the corresponding products and the only system to produce bis(coupling) products. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Heterocyclic quinones as pharmaceutical agents

Pyrrolylquinones and indolylquinones useful for treating diseases such as neurodegenerative disease, viral infections and proliferative disease are described, along with methods of making such compounds and pharmaceutical formulations containing such comp

Synthesis of 2,5-dihydroxy-3-(indol-3-yl)benzoquinones by acid-catalyzed condensation of indoles with 2,5-dichlorobenzoquinone

Three methods for the conjugate addition of indoles to 2,5-dichlorobenzoquinone have been developed. A wide variety of indoles substituted with halogen, alkyl, alkoxy, and aryl groups participate in anaerobic condensation reactions promoted by HCl, H2SO4, or CH3CO2H. The hydroquinone product is partially oxidized by excess dichlorobenzoquinone and fully converted to the 2,5-dichloro-3-(indol-3-yl)benzoquinone targets by DDQ or Ag2CO3 oxidation. 2,5-Dihydroxy- 3-(indol-3-yl)benzoquinones can be obtained from the dichlorides by alkaline hydrolysis. The rotational characteristics of the biaryl bond created in these reactions have been examined by theoretical and spectroscopic methods.

Synthesis of 3-Indolyl-2,5-dihydroxybenzoquinones

(Matrix Presented) 3-Indolylquinones can be efficiently prepared by the acid-catalyzed condensation of indoles with 2,5-dichlorobenzoquinone, followed by DDQ oxidation. The resulting dichloroquinones are hydrolyzed to the 3-indolyldihydroxybenzoquinones.