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Direct Oxidative Coupling Of N-actylindoles With Anisoles Using Hypervalent Iodine Reagents And Palladium-catalyzed Sequential Cyclization/coupling Reaction

Posted on:2011-10-31Degree:MasterType:Thesis
Country:ChinaCandidate:D W WangFull Text:PDF
GTID:2121360308955431Subject:Organic Chemistry
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Heterocyclic compounds are most important compounds in organic chemistry, Among them, indole, furan, and quinoline are most privileged structul motif widely distributed in natural products. Some of these heterocyclic compounds exhibited important biological activity, chemistry activities of plants and animals, and have great value in medicinal and agricultural.The study of utilizing hypervalent iodine compounds in new types of organic reactions are carried out rapidly in recent years. As metal-free oxidantive reagents, hypervalent iodine reagents have great value in organic synthesis. In the presence of hypervalent iodine reagents (PIFA), Direct coupling reaction of N-acetyl-indole with aromatic compounds provided C-3 arylated indoles in high regioselectivity. Compared with the heavy metal catalyzed cross-coupling reactions our research have many advantages, such as the high regioselectivity, the low toxicity of oxidant (PIFA), and the mild reaction conditions.Palladium-catalyzed reactions is also a hot topic of current research. We studied the cyclization and coupling reactions of substituted indoles with (2-bromoethynyl)-2-methoxybenzene in the presence of palladium catalyst. The reaction realized one pot sequentive coupling/cyclization, and produced benzofuran. The advantages of reaction included mild reaction conditions and simple experimental procedures. Our work will provide a new way to synthesize the heterocyclic compounds which have similar structures.Quinolones is a widely used antibiotics. Yaequinolones have a quinolone core, and extracted from metabolites of penicillium, have good insecticidal, fungicidal activity. We completed multi-step reactions using simple, inexpensive materials, and prepared the important intermediate by two routes. Attempts towards the synthesis of the target molecule were carried out in this work.
Keywords/Search Tags:indole, anisole, benzofuran, hypervalent iodine reagents, oxidative coupling, palladium-catalyzed, quinolone, synthesis
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