Formal [4+2]-annulation of vinyl azides with N-unsaturated aldimines
Highly functionalized quinolines and pyridines could be synthesized by BF3⋅OEt2-mediated reactions of vinyl azides with N-aryl and N-alkenyl aldimines, respectively. The reaction mechanism could be characterized as formal [4+2]-annulation, including unprecedented enamine-type nucleophilic attack of...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2014
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/105127 http://hdl.handle.net/10220/20689 http://dx.doi.org/10.1002/asia.201402421 |
| _version_ | 1811682248270807040 |
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| author | Zhu, Xu Wang, Yi-Feng Zhang, Feng-Lian Chiba, Shunsuke |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Zhu, Xu Wang, Yi-Feng Zhang, Feng-Lian Chiba, Shunsuke |
| author_sort | Zhu, Xu |
| collection | NTU |
| description | Highly functionalized quinolines and pyridines could be synthesized by BF3⋅OEt2-mediated reactions of vinyl azides with N-aryl and N-alkenyl aldimines, respectively. The reaction mechanism could be characterized as formal [4+2]-annulation, including unprecedented enamine-type nucleophilic attack of vinyl azides to aldimines and subsequent nucleophilic cyclization onto the resulting iminodiazonium ion moieties. |
| first_indexed | 2024-10-01T03:53:49Z |
| format | Journal Article |
| id | ntu-10356/105127 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:53:49Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-10356/1051272019-12-06T21:46:21Z Formal [4+2]-annulation of vinyl azides with N-unsaturated aldimines Zhu, Xu Wang, Yi-Feng Zhang, Feng-Lian Chiba, Shunsuke School of Physical and Mathematical Sciences DRNTU::Science::Physics::Atomic physics Highly functionalized quinolines and pyridines could be synthesized by BF3⋅OEt2-mediated reactions of vinyl azides with N-aryl and N-alkenyl aldimines, respectively. The reaction mechanism could be characterized as formal [4+2]-annulation, including unprecedented enamine-type nucleophilic attack of vinyl azides to aldimines and subsequent nucleophilic cyclization onto the resulting iminodiazonium ion moieties. 2014-09-15T05:46:48Z 2019-12-06T21:46:21Z 2014-09-15T05:46:48Z 2019-12-06T21:46:21Z 2014 2014 Journal Article Zhu, X., Wang, Y.-F., Zhang, F.-L., & Chiba, S. (2014). Formal [4+2]-annulation of vinyl azides with N-unsaturated aldimines. Chemistry - an Asian journal, 9(9), 2458-2462. 1861-4728 https://hdl.handle.net/10356/105127 http://hdl.handle.net/10220/20689 http://dx.doi.org/10.1002/asia.201402421 en Chemistry - an Asian journal © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Physics::Atomic physics Zhu, Xu Wang, Yi-Feng Zhang, Feng-Lian Chiba, Shunsuke Formal [4+2]-annulation of vinyl azides with N-unsaturated aldimines |
| title | Formal [4+2]-annulation of vinyl azides with N-unsaturated aldimines |
| title_full | Formal [4+2]-annulation of vinyl azides with N-unsaturated aldimines |
| title_fullStr | Formal [4+2]-annulation of vinyl azides with N-unsaturated aldimines |
| title_full_unstemmed | Formal [4+2]-annulation of vinyl azides with N-unsaturated aldimines |
| title_short | Formal [4+2]-annulation of vinyl azides with N-unsaturated aldimines |
| title_sort | formal 4 2 annulation of vinyl azides with n unsaturated aldimines |
| topic | DRNTU::Science::Physics::Atomic physics |
| url | https://hdl.handle.net/10356/105127 http://hdl.handle.net/10220/20689 http://dx.doi.org/10.1002/asia.201402421 |
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