Synthesis and intramolecular ring transformation of N,N′-dialkylated 2,6,9-triazabicyclo[3.3.1]nonadienes

Yumi Nakaike; Yusuke Yoshida; Soichi Yokoyama; Akitaka Ito; Nagatoshi Nishiwaki

doi:10.1039/D0OB01950J

Synthesis and intramolecular ring transformation of N,N′-dialkylated 2,6,9-triazabicyclo[3.3.1]nonadienes†

Yumi Nakaike,

^a Yusuke Yoshida,^b Soichi Yokoyama,

^bcd Akitaka Ito

^bc and Nagatoshi Nishiwaki

*^bc

Author affiliations

* Corresponding authors

^a Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Yoshidahonmachi, Sakyo-ku, Kyoto 606-8501, Japan

^b School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan
E-mail: nishiwaki.nagatoshi@kochi-tech.ac.jp

^c Research Center for Molecular Design, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan

^d The Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047, Japan

Abstract

The first and facile synthesis of N,N′-dialkylated 2,6,9-triazabicyclo[3.3.1]nonadienes was achieved by the [4 + 4] self-condensation of β-formyl-β-nitroenamine in the presence of ammonium acetate. The 2,6- and 2,9-dialkylated products were found to be interconvertible when dissolved in a solvent. This isomerization proceeds through intramolecular ring transformation via a common intermediate under equilibrium.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/D0OB01950J
Article type: Paper
Submitted: 23 Sep 2020
Accepted: 28 Oct 2020
First published: 28 Oct 2020
This article is Open Access

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Org. Biomol. Chem., 2020,18, 9109-9116

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Synthesis and intramolecular ring transformation of N,N′-dialkylated 2,6,9-triazabicyclo[3.3.1]nonadienes

Y. Nakaike, Y. Yoshida, S. Yokoyama, A. Ito and N. Nishiwaki, Org. Biomol. Chem., 2020, 18, 9109 DOI: 10.1039/D0OB01950J

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Organic & Biomolecular Chemistry

Synthesis and intramolecular ring transformation of N,N′-dialkylated 2,6,9-triazabicyclo[3.3.1]nonadienes†

Abstract

Supplementary files

Article information

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Synthesis and intramolecular ring transformation of N,N′-dialkylated 2,6,9-triazabicyclo[3.3.1]nonadienes

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