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

Xu Zhu; Yi Feng Wang; Feng Lian Zhang; Shunsuke Chiba

doi:10.1002/asia.201402421

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

Xu Zhu, Yi Feng Wang, Feng Lian Zhang, Shunsuke Chiba^*

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

Abstract

Highly functionalized quinolines and pyridines could be synthesized by BF₃̇OEt₂-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.

Original language	English
Pages (from-to)	2458-2462
Number of pages	5
Journal	Chemistry - An Asian Journal
Volume	9
Issue number	9
DOIs	https://doi.org/10.1002/asia.201402421
Publication status	Published - Sept 2014
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
General Chemistry
Organic Chemistry

Keywords

annulation
azides
heterocycles
Lewis acids

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10.1002/asia.201402421

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abstract = "Highly functionalized quinolines and pyridines could be synthesized by BF{\.3}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.",

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AU - Zhu, Xu

AU - Wang, Yi Feng

AU - Zhang, Feng Lian

AU - Chiba, Shunsuke

PY - 2014/9

Y1 - 2014/9

N2 - Highly functionalized quinolines and pyridines could be synthesized by BF3̇OEt2-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.

AB - Highly functionalized quinolines and pyridines could be synthesized by BF3̇OEt2-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.

KW - annulation

KW - azides

KW - heterocycles

KW - Lewis acids

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JF - Chemistry - An Asian Journal

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

Abstract

ASJC Scopus Subject Areas

Keywords

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