329015-22-7Relevant academic research and scientific papers
"On water"-promoted direct coupling of indoles with 1,4-benzoquinones without catalyst
Zhang, Hai-Bo,Liu, Li,Chen, Yong-Jun,Wang, Dong,Li, Chao-Jun
, p. 869 - 873 (2007/10/03)
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
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Page/Page column 9, (2008/06/13)
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
Pirrung, Michael C.,Deng, Liu,Li, Zhitao,Park, Kaapjoo
, p. 8374 - 8388 (2007/10/03)
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
Pirrung, Michael C.,Park, Kaapjoo,Li, Zhitao
, p. 365 - 367 (2007/10/03)
(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.
