Synthesis of pyridines via [4 + 2] cycloadditions of vinylallenes with azadienophiles
Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2015.
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| Format: | Thesis |
| Language: | eng |
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Massachusetts Institute of Technology
2016
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| Online Access: | http://hdl.handle.net/1721.1/101546 |
| _version_ | 1811084474638663680 |
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| author | Hamzik, Philip J. (Philip Jonathan) |
| author2 | Massachusetts Institute of Technology. Department of Chemistry. |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry. Hamzik, Philip J. (Philip Jonathan) |
| author_sort | Hamzik, Philip J. (Philip Jonathan) |
| collection | MIT |
| description | Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2015. |
| first_indexed | 2024-09-23T12:51:22Z |
| format | Thesis |
| id | mit-1721.1/101546 |
| institution | Massachusetts Institute of Technology |
| language | eng |
| last_indexed | 2024-09-23T12:51:22Z |
| publishDate | 2016 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/1015462019-04-11T01:15:29Z Synthesis of pyridines via [4 + 2] cycloadditions of vinylallenes with azadienophiles Hamzik, Philip J. (Philip Jonathan) Massachusetts Institute of Technology. Department of Chemistry. Massachusetts Institute of Technology. Department of Chemistry. Chemistry. Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2015. Cataloged from PDF version of thesis. Includes bibliographical references. Pyridines are an important class of heterocycle with widespread applications. However, the efficient preparation of substituted pyridines remains a challenge in organic synthesis. This thesis describes new annulation strategies for the synthesis of highly substituted pyridines that involve [4 + 2] cycloadditions of vinylallenes with azadienophiles. Part II of this thesis describes a unimolecular, formal [2 + 2 + 2] cycloaddition strategy for the synthesis of tricyclic pyridines based on intramolecular propargylic ene/imino Diels-Alder reaction cascades. In this variant, unactivated oximino ethers and NN-dialkylhydrazones function as dienophiles in thermal Diels-Alder reactions. Part III of this thesis describes strategies for the synthesis of bicyclic and monocyclic 2-sulfonylpyrdines based on [4 + 2] cycloadditions of vinylallenes with tosyl cyanide. In addition, Part III discusses the synthetic elaboration of these 2- sulfonylpyridines via nucleophilic aromatic substitution reactions. Overall, annulation strategies based on [4 + 2] cycloadditions of vinylallenes with azadienophiles have been developed for the preparation of highly substituted pyridines in an efficient, convergent, and regioselective fashion. by Philip J. Hamzik. Ph. D. 2016-03-03T21:08:04Z 2016-03-03T21:08:04Z 2015 2015 Thesis http://hdl.handle.net/1721.1/101546 940564717 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 293 pages application/pdf Massachusetts Institute of Technology |
| spellingShingle | Chemistry. Hamzik, Philip J. (Philip Jonathan) Synthesis of pyridines via [4 + 2] cycloadditions of vinylallenes with azadienophiles |
| title | Synthesis of pyridines via [4 + 2] cycloadditions of vinylallenes with azadienophiles |
| title_full | Synthesis of pyridines via [4 + 2] cycloadditions of vinylallenes with azadienophiles |
| title_fullStr | Synthesis of pyridines via [4 + 2] cycloadditions of vinylallenes with azadienophiles |
| title_full_unstemmed | Synthesis of pyridines via [4 + 2] cycloadditions of vinylallenes with azadienophiles |
| title_short | Synthesis of pyridines via [4 + 2] cycloadditions of vinylallenes with azadienophiles |
| title_sort | synthesis of pyridines via 4 2 cycloadditions of vinylallenes with azadienophiles |
| topic | Chemistry. |
| url | http://hdl.handle.net/1721.1/101546 |
| work_keys_str_mv | AT hamzikphilipjphilipjonathan synthesisofpyridinesvia42cycloadditionsofvinylalleneswithazadienophiles |