Hydroxysulfonylation of Quinones with Aryl(alkyl)sulfonyl Hydrazides for the Synthesis of 1,4-Dihydroxy-2- aryl(alkyl)sulfonylbenzenes

摘要

β-Ketoacyl-ACP-synthase III (FabH) plays an important role in bacterial fatty-acid biosynthesis as an important condensing enzyme. 1,4-Dihydroxy-2-tosylnaphthalene and its analogues are potent inhibitors of FabH. Traditional methods for the synthesis of these compounds still suffer from some drawbacks. In this work, an efficient copper-catalyzed method for the hydroxysulfonylation of quinones with aryl(alkyl)sulfonyl hydrazides was developed for the direct synthesis of 1,4-dihydroxy- 2-phenylsufonylbenzenes. A series of biologically useful FabH inhibitors were obtained in good yields under argon. Both aryl and alkyl substituents were well tolerated in the reaction.