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

MC Pirrung, L Deng, Z Li, K Park

文献索引：Pirrung, Michael C.; Deng, Liu; Li, Zhitao; Park, Kaapjoo Journal of Organic Chemistry, 2002 , vol. 67, # 24 p. 8374 - 8388

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被引用次数: 51

摘要

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 ...