Synthesis of highly substituted benzo-fused nitrogen heterocycles via tandem benzannulation/cyclization strategies
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2013.
| Main Author: | |
|---|---|
| Other Authors: | |
| Format: | Thesis |
| Language: | eng |
| Published: |
Massachusetts Institute of Technology
2014
|
| Subjects: | |
| Online Access: | http://hdl.handle.net/1721.1/84379 |
| _version_ | 1826202426576732160 |
|---|---|
| author | Willumstad, Thomas P. (Thomas Paul) |
| author2 | Rick L. Danheiser. |
| author_facet | Rick L. Danheiser. Willumstad, Thomas P. (Thomas Paul) |
| author_sort | Willumstad, Thomas P. (Thomas Paul) |
| collection | MIT |
| description | Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2013. |
| first_indexed | 2024-09-23T12:07:17Z |
| format | Thesis |
| id | mit-1721.1/84379 |
| institution | Massachusetts Institute of Technology |
| language | eng |
| last_indexed | 2024-09-23T12:07:17Z |
| publishDate | 2014 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/843792019-11-22T04:14:44Z Synthesis of highly substituted benzo-fused nitrogen heterocycles via tandem benzannulation/cyclization strategies Willumstad, Thomas P. (Thomas Paul) Rick L. Danheiser. Massachusetts Institute of Technology. Department of Chemistry. Massachusetts Institute of Technology. Department of Chemistry. Chemistry. Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2013. Cataloged from PDF version of thesis. Includes bibliographical references. 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. by Thomas P. Willumstad. Ph.D. 2014-01-23T18:40:10Z 2014-01-23T18:40:10Z 2013 2013 Thesis http://hdl.handle.net/1721.1/84379 867637770 eng 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 345 pages application/pdf Massachusetts Institute of Technology |
| spellingShingle | Chemistry. Willumstad, Thomas P. (Thomas Paul) Synthesis of highly substituted benzo-fused nitrogen heterocycles via tandem benzannulation/cyclization strategies |
| title | Synthesis of highly substituted benzo-fused nitrogen heterocycles via tandem benzannulation/cyclization strategies |
| title_full | Synthesis of highly substituted benzo-fused nitrogen heterocycles via tandem benzannulation/cyclization strategies |
| title_fullStr | Synthesis of highly substituted benzo-fused nitrogen heterocycles via tandem benzannulation/cyclization strategies |
| title_full_unstemmed | Synthesis of highly substituted benzo-fused nitrogen heterocycles via tandem benzannulation/cyclization strategies |
| title_short | Synthesis of highly substituted benzo-fused nitrogen heterocycles via tandem benzannulation/cyclization strategies |
| title_sort | synthesis of highly substituted benzo fused nitrogen heterocycles via tandem benzannulation cyclization strategies |
| topic | Chemistry. |
| url | http://hdl.handle.net/1721.1/84379 |
| work_keys_str_mv | AT willumstadthomaspthomaspaul synthesisofhighlysubstitutedbenzofusednitrogenheterocyclesviatandembenzannulationcyclizationstrategies |