Catalytic and Stoichiometric Synthesis of Novel 3-Aminocarbonyl-, 3-Alkoxycarbonyl-, and 3-Amino-4-indolylmaleimides

Novel nonsymmetrically substituted 4-indolylmaleimides have been synthesized via palladium-catalyzed alkoxy- and aminocarbonylation of 3-bromo-1-methyl-4-(2-methyl-3-indolyl)maleimide (1) with alcohols and amines in the presence of carbon monoxide. The resulting carboxamide derivatives represent a new class of potentially bioactive compounds. In addition, the direct amination reaction of 1 proceeded smoothly in the absence of catalyst and gave the desired 3-amino-4-indolylmaleimides in good yields. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)