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dc.contributor.authorHamzik, Philip J. (Philip Jonathan)en_US
dc.contributor.otherMassachusetts Institute of Technology. Department of Chemistry.en_US
dc.date.accessioned2016-03-03T21:08:04Z
dc.date.available2016-03-03T21:08:04Z
dc.date.copyright2015en_US
dc.date.issued2015en_US
dc.identifier.urihttp://hdl.handle.net/1721.1/101546
dc.descriptionThesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2015.en_US
dc.descriptionCataloged from PDF version of thesis.en_US
dc.descriptionIncludes bibliographical references.en_US
dc.description.abstractPyridines are an important class of heterocycle with widespread applications. However, the efficient preparation of substituted pyridines remains a challenge in organic synthesis. This thesis describes new annulation strategies for the synthesis of highly substituted pyridines that involve [4 + 2] cycloadditions of vinylallenes with azadienophiles. Part II of this thesis describes a unimolecular, formal [2 + 2 + 2] cycloaddition strategy for the synthesis of tricyclic pyridines based on intramolecular propargylic ene/imino Diels-Alder reaction cascades. In this variant, unactivated oximino ethers and NN-dialkylhydrazones function as dienophiles in thermal Diels-Alder reactions. Part III of this thesis describes strategies for the synthesis of bicyclic and monocyclic 2-sulfonylpyrdines based on [4 + 2] cycloadditions of vinylallenes with tosyl cyanide. In addition, Part III discusses the synthetic elaboration of these 2- sulfonylpyridines via nucleophilic aromatic substitution reactions. Overall, annulation strategies based on [4 + 2] cycloadditions of vinylallenes with azadienophiles have been developed for the preparation of highly substituted pyridines in an efficient, convergent, and regioselective fashion.en_US
dc.description.statementofresponsibilityby Philip J. Hamzik.en_US
dc.format.extent293 pagesen_US
dc.language.isoengen_US
dc.publisherMassachusetts Institute of Technologyen_US
dc.rightsM.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission.en_US
dc.rights.urihttp://dspace.mit.edu/handle/1721.1/7582en_US
dc.subjectChemistry.en_US
dc.titleSynthesis of pyridines via [4 + 2] cycloadditions of vinylallenes with azadienophilesen_US
dc.typeThesisen_US
dc.description.degreePh. D.en_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistry.en_US
dc.identifier.oclc940564717en_US


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