329015-20-5Relevant articles and documents
"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.
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.