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
Name
940566426-MIT.pdf
Description
Full printable version
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13.19 MB
Format
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Checksum (MD5)
c70f6aa08cbd2d7857e5ef89ca29bada
Author(s)
Wang, Yu-Pu, Ph. D. Massachusetts Institute of Technology
Alternative Title
[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
Date Issued
2015
Publisher
Massachusetts Institute of Technology
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.
Description
Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2015.
Cataloged from PDF version of thesis.
Includes bibliographical references.
Subjects
Chemistry.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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