Synthesis of highly substituted benzo-fused nitrogen heterocycles via tandem benzannulation/cyclization strategies
Name
867637770-MIT.pdf
Description
Full printable version
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23.09 MB
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Adobe PDF
Checksum (MD5)
3b8f9576a6bcd940e2c39d4b56f04577
Author(s)
Willumstad, Thomas P. (Thomas Paul)
Advisor(s)
Rick L. Danheiser.
Date Issued
2013
Publisher
Massachusetts Institute of Technology
Abstract
Benzannulations employing ynamides and vinylketenes (generated in situ from [alpha]-diazo ketones) were investigated. Irradiation of the diazo ketones using a batch or continuous-flow reactor leads to the formation of vinylketenes via a photo-Wolff rearrangement. The vinylketenes then react with ynamides via a pericyclic cascade process to produce highly substituted aniline derivatives. Using this vinylketene-based benzannulation, tandem strategies for the synthesis of highly substituted benzo-fused nitrogen heterocycles were investigated. A tandem benzannulation-iodocyclization method for the synthesis of polysubstituted quinolines was established. In addition, a tandem strategy for the synthesis of carbazoles was developed and applied in the total synthesis of the carbazole alkaloid carazostatin as well as formal syntheses of the alkaloids carbazoquinocin C and antiostatin A₄.
Description
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2013.
Cataloged from PDF version of thesis.
Includes bibliographical references.
Subjects
Chemistry.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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