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Issue 4, 2017
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Gold(i)-catalyzed 6-endo-dig azide–yne cyclization: efficient access to 2H-1,3-oxazines

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Abstract

Denitrogenative 6-endo-dig azide–yne cyclization of α-propargyloxy-β-haloalkylazides was enabled by gold catalysis, thus providing 2H-1,3-oxazines. This rare cyclization mode in gold-catalyzed reactions of azide–yne substrates was demonstrated to be facilitated and controlled by electronic and resonance effects of the alkyne substituents. Molecular transformations of the as-prepared 2H-1,3-oxazines were also investigated.

Graphical abstract: Gold(i)-catalyzed 6-endo-dig azide–yne cyclization: efficient access to 2H-1,3-oxazines

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Supplementary files

Article information


Submitted
18 Oct 2016
Accepted
10 Dec 2016
First published
13 Dec 2016

Chem. Commun., 2017,53, 736-739
Article type
Communication

Gold(I)-catalyzed 6-endo-dig azide–yne cyclization: efficient access to 2H-1,3-oxazines

G. H. Lonca, C. Tejo, H. L. Chan, S. Chiba and F. Gagosz, Chem. Commun., 2017, 53, 736
DOI: 10.1039/C6CC08397H

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