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...
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sg-ntu-dr.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. |
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DRNTU::Science::Physics::Atomic physics |
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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 |
| 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. |
| 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 |
| format |
Article |
| author |
Zhu, Xu Wang, Yi-Feng Zhang, Feng-Lian Chiba, Shunsuke |
| author_sort |
Zhu, Xu |
| title |
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_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_sort |
formal [4+2]-annulation of vinyl azides with n-unsaturated aldimines |
| publishDate |
2014 |
| url |
https://hdl.handle.net/10356/105127 http://hdl.handle.net/10220/20689 http://dx.doi.org/10.1002/asia.201402421 |
| _version_ |
1681037746281381888 |