Issue 8, 2014
From the journal:

Organic Chemistry Frontiers

N-Allenylnitrone acts as 2-azadiene in the Cu-catalyzed cascade reaction of O-propargylic oximes with azodicarboxylates†

Itaru Nakamura,*a   Takeru Jo,b   Dong Zhangb  and  Masahiro Teradaab  

* Corresponding authors

a Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
E-mail: itaru-n@m.tohoku.ac.jp

b Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan

Abstract

The reaction of O-propargylic oximes with azodicarboxylates efficiently afforded 1,2,4-triazine oxides in good yields. The key intermediate, N-allenylnitrone, acted as 2-azadiene, undergoing stepwise [4 + 2] cycloaddition.

Graphical abstract: N-Allenylnitrone acts as 2-azadiene in the Cu-catalyzed cascade reaction of O-propargylic oximes with azodicarboxylates

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Article information

DOI
https://doi.org/10.1039/C4QO00156G
Article type
Research Article
Submitted
27 May 2014
Accepted
04 Jul 2014
First published
07 Jul 2014

Org. Chem. Front., 2014,1, 914-918

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N-Allenylnitrone acts as 2-azadiene in the Cu-catalyzed cascade reaction of O-propargylic oximes with azodicarboxylates

I. Nakamura, T. Jo, D. Zhang and M. Terada, Org. Chem. Front., 2014, 1, 914 DOI: 10.1039/C4QO00156G

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