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

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

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Citation Number: 51

Abstract

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 ...