Tandem benzannulation-ring closing metathesis strategy for the synthesis of benzo-fused nitrogen heterocycles ;
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008.
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| Format: | Thesis |
| Language: | eng |
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Massachusetts Institute of Technology
2009
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| Online Access: | http://hdl.handle.net/1721.1/46034 |
| _version_ | 1826213334473506816 |
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| author | Mak, Xiao Yin |
| author2 | Rick L. Danheiser. |
| author_facet | Rick L. Danheiser. Mak, Xiao Yin |
| author_sort | Mak, Xiao Yin |
| collection | MIT |
| description | Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008. |
| first_indexed | 2024-09-23T15:47:25Z |
| format | Thesis |
| id | mit-1721.1/46034 |
| institution | Massachusetts Institute of Technology |
| language | eng |
| last_indexed | 2024-09-23T15:47:25Z |
| publishDate | 2009 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/460342019-04-10T23:13:40Z Tandem benzannulation-ring closing metathesis strategy for the synthesis of benzo-fused nitrogen heterocycles ; Formal synthesis of (+)-FR900482 Mak, Xiao Yin Rick L. Danheiser. Massachusetts Institute of Technology. Dept. of Chemistry. Massachusetts Institute of Technology. Dept. of Chemistry. Chemistry. Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008. Vita. Includes bibliographical references. A tandem benzannulation-ring closing metathesis strategy for the efficient synthesis of benzo-fused nitrogen heterocycles such as dihydroquinolines, benzazepines, and benzazocines has been developed. This strategy is based on the benzannulation reaction of ynamides with cyclobutenones or [alpha]-diazo ketones to generate highly-substituted aniline derivatives, which then participate in ring-closing metathesis reactions to form nitrogen heterocycles. The synthetic utility of this strategy has been demonstrated by its successful application in a formal synthesis of the natural product (+)-FR900482. In addition, an environmentally-friendly approach to the synthesis of amides and lactams has been developed using supercritical carbon dioxide as a 'green' replacement solvent. The amide products are generated from the addition of amines to ketenes, which are formed in situ from the retro-ene reaction of alkynyl ethers. by Xiao Yin Mak. Ph.D. 2009-06-30T17:06:15Z 2009-06-30T17:06:15Z 2008 2008 Thesis http://hdl.handle.net/1721.1/46034 367601332 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 2 v. (311 leaves) application/pdf Massachusetts Institute of Technology |
| spellingShingle | Chemistry. Mak, Xiao Yin Tandem benzannulation-ring closing metathesis strategy for the synthesis of benzo-fused nitrogen heterocycles ; |
| title | Tandem benzannulation-ring closing metathesis strategy for the synthesis of benzo-fused nitrogen heterocycles ; |
| title_full | Tandem benzannulation-ring closing metathesis strategy for the synthesis of benzo-fused nitrogen heterocycles ; |
| title_fullStr | Tandem benzannulation-ring closing metathesis strategy for the synthesis of benzo-fused nitrogen heterocycles ; |
| title_full_unstemmed | Tandem benzannulation-ring closing metathesis strategy for the synthesis of benzo-fused nitrogen heterocycles ; |
| title_short | Tandem benzannulation-ring closing metathesis strategy for the synthesis of benzo-fused nitrogen heterocycles ; |
| title_sort | tandem benzannulation ring closing metathesis strategy for the synthesis of benzo fused nitrogen heterocycles |
| topic | Chemistry. |
| url | http://hdl.handle.net/1721.1/46034 |
| work_keys_str_mv | AT makxiaoyin tandembenzannulationringclosingmetathesisstrategyforthesynthesisofbenzofusednitrogenheterocycles AT makxiaoyin formalsynthesisoffr900482 |