Oxidative cyclization of unsaturated aminoquinones. Synthesis of quinolinoquinones. Palladium-catalyzed synthesis of pyrroloindoloquinones

PR Weider, LS Hegedus, H Asada

Index: Weider, Paul R.; Hegedus, Louis S.; Asada, Hideki; D'Andreq, Stanley V. Journal of Organic Chemistry, 1985 , vol. 50, # 22 p. 4276 - 4281

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Citation Number: 62

Abstract

2-Allyl-3, 6-diamino-5-methyl-1, 4-benzoquinone (1) underwent a facile oxidative cyclization to produce quinolinoquinone 3 in the presence of a variety of oxidizing agents, including palladium (I1) salts. Chloranil was the most efficient oxidizing agent and produced 3 in high yield. Under hydrolysis conditions,(hydroxyethyl) benzobis (oxazole) 4 underwent a retroaldol reaction, followed by an aldehyde amine condensation and an electrocyclic ...