Synthesis of azaheterocycles by Cu-catalyzed aerobic alkene diamination and tempo-mediated aliphatic C-H oxidation
Due to the significance of nitrogen-containing heterocycles (azaheterocycles) in biology, medicine and materials science, it is important to invent robust methodologies for synthesis of azaheterocycles using readily available nitrogen-containing starting materials in unprecedented fashions. This the...
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| Format: | Thesis |
| Language: | English |
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2015
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| Online Access: | http://hdl.handle.net/10356/65740 |
| _version_ | 1811690322064834560 |
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| author | Zhu, Xu |
| author2 | Chiba Shunsuke |
| author_facet | Chiba Shunsuke Zhu, Xu |
| author_sort | Zhu, Xu |
| collection | NTU |
| description | Due to the significance of nitrogen-containing heterocycles (azaheterocycles) in biology, medicine and materials science, it is important to invent robust methodologies for synthesis of azaheterocycles using readily available nitrogen-containing starting materials in unprecedented fashions. This thesis describes methodology development for synthesis of azaheterocycles using intramolecular tactics by 1) copper-catalyzed aerobic synthesis of bi- and tricyclic amidines via intramolecular diamination of acyclic N1-pentenylamidines, and 2) TEMPO-mediated remote aliphatic C–H oxidation (oxygenation and amination) with oximes and hydrazones as the corresponding O- and N-radical precursors, respectively. This operationally simple process enables the concise assembly of substituted isoxazole, pyrazole, and hydropyridazine skeletons |
| first_indexed | 2024-10-01T06:02:09Z |
| format | Thesis |
| id | ntu-10356/65740 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:02:09Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-10356/657402023-02-28T23:48:01Z Synthesis of azaheterocycles by Cu-catalyzed aerobic alkene diamination and tempo-mediated aliphatic C-H oxidation Zhu, Xu Chiba Shunsuke School of Physical and Mathematical Sciences DRNTU::Science::Chemistry Due to the significance of nitrogen-containing heterocycles (azaheterocycles) in biology, medicine and materials science, it is important to invent robust methodologies for synthesis of azaheterocycles using readily available nitrogen-containing starting materials in unprecedented fashions. This thesis describes methodology development for synthesis of azaheterocycles using intramolecular tactics by 1) copper-catalyzed aerobic synthesis of bi- and tricyclic amidines via intramolecular diamination of acyclic N1-pentenylamidines, and 2) TEMPO-mediated remote aliphatic C–H oxidation (oxygenation and amination) with oximes and hydrazones as the corresponding O- and N-radical precursors, respectively. This operationally simple process enables the concise assembly of substituted isoxazole, pyrazole, and hydropyridazine skeletons Doctor of Philosophy (SPMS) 2015-12-11T01:57:41Z 2015-12-11T01:57:41Z 2015 2015 Thesis Zhu, X. (2015). Synthesis of azaheterocycles by Cu-catalyzed aerobic alkene diamination and tempo-mediated aliphatic C-H oxidation. Doctoral thesis, Nanyang Technological University, Singapore. http://hdl.handle.net/10356/65740 en 223 p. application/pdf |
| spellingShingle | DRNTU::Science::Chemistry Zhu, Xu Synthesis of azaheterocycles by Cu-catalyzed aerobic alkene diamination and tempo-mediated aliphatic C-H oxidation |
| title | Synthesis of azaheterocycles by Cu-catalyzed aerobic alkene diamination and tempo-mediated aliphatic C-H oxidation |
| title_full | Synthesis of azaheterocycles by Cu-catalyzed aerobic alkene diamination and tempo-mediated aliphatic C-H oxidation |
| title_fullStr | Synthesis of azaheterocycles by Cu-catalyzed aerobic alkene diamination and tempo-mediated aliphatic C-H oxidation |
| title_full_unstemmed | Synthesis of azaheterocycles by Cu-catalyzed aerobic alkene diamination and tempo-mediated aliphatic C-H oxidation |
| title_short | Synthesis of azaheterocycles by Cu-catalyzed aerobic alkene diamination and tempo-mediated aliphatic C-H oxidation |
| title_sort | synthesis of azaheterocycles by cu catalyzed aerobic alkene diamination and tempo mediated aliphatic c h oxidation |
| topic | DRNTU::Science::Chemistry |
| url | http://hdl.handle.net/10356/65740 |
| work_keys_str_mv | AT zhuxu synthesisofazaheterocyclesbycucatalyzedaerobicalkenediaminationandtempomediatedaliphaticchoxidation |