Formal [4+2]-annulation of vinyl azides with N-unsaturated aldimines

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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Main Authors: Zhu, Xu, Wang, Yi-Feng, Zhang, Feng-Lian, Chiba, Shunsuke
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
Subjects:
DRNTU::Science::Physics::Atomic physics
Online Access:https://hdl.handle.net/10356/105127
http://hdl.handle.net/10220/20689
http://dx.doi.org/10.1002/asia.201402421
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Institution: Nanyang Technological University
Language: English
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spelling 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.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Physics::Atomic physics
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
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

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