| dc.contributor.advisor | Rick L. Danheiser. | en_US |
| dc.contributor.author | Willumstad, Thomas P. (Thomas Paul) | en_US |
| dc.contributor.other | Massachusetts Institute of Technology. Department of Chemistry. | en_US |
| dc.date.accessioned | 2014-01-23T18:40:10Z | |
| dc.date.available | 2014-01-23T18:40:10Z | |
| dc.date.copyright | 2013 | en_US |
| dc.date.issued | 2013 | en_US |
| dc.identifier.uri | http://hdl.handle.net/1721.1/84379 | |
| dc.description | Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2013. | en_US |
| dc.description | Cataloged from PDF version of thesis. | en_US |
| dc.description | Includes bibliographical references. | en_US |
| dc.description.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. | en_US |
| dc.description.statementofresponsibility | by Thomas P. Willumstad. | en_US |
| dc.format.extent | 345 pages | en_US |
| dc.language.iso | eng | en_US |
| dc.publisher | Massachusetts Institute of Technology | en_US |
| dc.rights | 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. | en_US |
| dc.rights.uri | http://dspace.mit.edu/handle/1721.1/7582 | en_US |
| dc.subject | Chemistry. | en_US |
| dc.title | Synthesis of highly substituted benzo-fused nitrogen heterocycles via tandem benzannulation/cyclization strategies | en_US |
| dc.type | Thesis | en_US |
| dc.description.degree | Ph.D. | en_US |
| dc.contributor.department | Massachusetts Institute of Technology. Department of Chemistry | |
| dc.identifier.oclc | 867637770 | en_US |
