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Novel And Direct Transformation Of Primary Amide And Synthesis Of Oxazole Heterocyclic Compounds

Posted on:2012-03-31Degree:MasterType:Thesis
Country:ChinaCandidate:J Y DingFull Text:PDF
GTID:2181330335468256Subject:Organic Chemistry
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Organic functional transformation is one of the most important parts in the organic synthesis. Environmentally friendly, simple, highly efficient and atomic-economic method is the new trend of synthetic organic chemistry. Recently, the American Chemical Society Green Chemistry Institute Pharmaceutical Roundtable identified amide formation as one of the most utilized and problematic syntheses in the pharmaceutical industry and as such has been labeled as a high priority research area. Based on these proofs, firstly, we expound the present research about amide formation. Secondly, we record the direct transformation from methyl ketones to primary amides in the enviromental friendly solvent-water. Next, we expand the scope of the substrates to get more secondary or tertiary amides. Finally, we investigate the side reaction about the amide formation.In chapter 1, as amides are one of the most prevalent fouctional groups both in nature and in Pharmaceuticals, their synthesis is numerous. Herein, we present the classic synthesis methods, name reactions and many new researches about amide formations.In chapter 2, as we know the significance of the amide, a novel and direct approach to primary amide compounds in the presence of iodine and aqueous ammonia has been developed in aqueous media. A possible tandem Lieben-Haller-Bauer reaction mechanism is proposed.In chapter 3, we expand the scope of the substrates to get more secondary or tertiary amides. Based on these, we prove the Lieben-Haller-Bauer reaction mechanism more exactly.In chapter 4, we investigate the side reaction about the amide formation. When we add some metal oxides, oxazole products can be detected. The reaction mechanism was proposed. And the structures of the compounds IV-22b and IV-22c were further confirmed by X-ray single crystal diffraction.
Keywords/Search Tags:iodine, amide, water, Lieben iodoform reaction, Haller-Bauer reaction
PDF Full Text Request
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