An unexpected synthesis of 7-azidofurazano[3,4-b]tetrazolopyrazine |
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Authors: | S Guillou F Terrier |
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Institution: | a Institut Lavoisier de Versailles, CNRS 8180, avenue des Etats-Unis, 78000 Versailles, France b SME, Centre de Recherches du Bouchet, rue Lavoisier, 91710 Vert-Le-Petit, France |
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Abstract: | In the course of our program focused on the preparation of high-nitrogen content heterocyclic compounds, we wish to report an original synthesis of the tricyclic 7-azidofurazano3,4-b]tetrazolopyrazine via an unprecedented reaction between 2,6-dimethoxy-3,5-dinitropyrazine and hydrazine hydrate. This compound was identified by an X-ray diffraction analysis. Further studies of its structure by 15N and 13C NMR spectroscopy were carried out in different solvents. This allowed us to observe a noteworthy equilibrium involving three forms resulting from the reversible opening of a tetrazole ring. |
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Keywords: | Pyrazine Nucleophilic substitution Azide Tetrazole Tautomerism 1H 13C and 15N NMR |
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