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Wang, Yu-Pu, Ph. D. Massachusetts Institute of Technology Massachusetts Institute of Technology. Department of Chemistry. Massachusetts Institute of Technology. Department of Chemistry 2016-03-03T21:08:43Z 2016-03-03T21:08:43Z 2015 2015 http://hdl.handle.net/1721.1/101556 940566426 Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2015. Cataloged from PDF version of thesis. Includes bibliographical references. The synthesis and reactions of 2-iodoynamides were investigated. 2-Iodoynamides undergo efficient and regioselective [2 + 2] cycloaddition with ketene to produce cyclobutenones that are useful synthetic building blocks. Reaction of 2-iodoynamides and vinylketenes generated in situ from cyclobutenones proceeds via a pericyclic cascade mechanism to produce highly substituted 2-iodoanilines. Tandem strategies for the synthesis of highly substituted indoles involving this benzannulation reaction were investigated. In addition, the synthesis of furo[2,3-g]thieno[2,3- e]indole, a new tetracyclic aromatic compound, was achieved via a strategy based on benzannulation with ynamides. by Yu-Pu Wang. Ph.D. 287 pages eng Massachusetts Institute of Technology M.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. http://dspace.mit.edu/handle/1721.1/7582 Chemistry. I. [2 +2] Cycloaddition and benzannulation of 2-iodoynamides and application to the construction of highly substituted indoles : II. Synthesis of furo[2,3-g]thieno[2,3-e]indole via a benzannulation strategy [2 +2] Cycloaddition and benzannulation of 2-iodoynamides and application to the construction of highly substituted indoles Synthesis of furo[2,3-g]thieno[2,3-e]indole via a benzannulation strategy Thesis application/pdf false Publication unknown unknown <Publication xmlns="https://www.openaire.eu/cerif-profile/1.1/" id="baf56ffe-7314-45ed-8529-3845462580c0"> <Type xmlns="https://www.openaire.eu/cerif-profile/vocab/COAR_Publication_Types">http://purl.org/coar/resource_type/c_1843</Type> <Language>eng</Language> <Title>I. [2 +2] Cycloaddition and benzannulation of 2-iodoynamides and application to the construction of highly substituted indoles : II. Synthesis of furo[2,3-g]thieno[2,3-e]indole via a benzannulation strategy</Title> <Subtitle>[2 +2] Cycloaddition and benzannulation of 2-iodoynamides and application to the construction of highly substituted indoles</Subtitle> <Subtitle>Synthesis of furo[2,3-g]thieno[2,3-e]indole via a benzannulation strategy</Subtitle> <PublishedIn> <Publication> </Publication> </PublishedIn> <PublicationDate>2015</PublicationDate> <Authors> <Author> <DisplayName>Wang, Yu-Pu, Ph. D. Massachusetts Institute of Technology</DisplayName> <Affiliation> <OrgUnit> </OrgUnit> </Affiliation> </Author> </Authors> <Editors> </Editors> <Publishers> <Publisher> <DisplayName>Massachusetts Institute of Technology</DisplayName> <OrgUnit /> </Publisher> </Publishers> <License>http://dspace.mit.edu/handle/1721.1/7582</License> <Keyword>Chemistry.</Keyword> <Abstract>The synthesis and reactions of 2-iodoynamides were investigated. 2-Iodoynamides undergo efficient and regioselective [2 + 2] cycloaddition with ketene to produce cyclobutenones that are useful synthetic building blocks. Reaction of 2-iodoynamides and vinylketenes generated in situ from cyclobutenones proceeds via a pericyclic cascade mechanism to produce highly substituted 2-iodoanilines. Tandem strategies for the synthesis of highly substituted indoles involving this benzannulation reaction were investigated. In addition, the synthesis of furo[2,3-g]thieno[2,3- e]indole, a new tetracyclic aromatic compound, was achieved via a strategy based on benzannulation with ynamides.</Abstract> <Access xmlns="http://purl.org/coar/access_right" > </Access> </Publication>