An unexpected synthesis of 7-azidofurazano[3,4-b]tetrazolopyrazine
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-azidofurazano[3,4-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.
Guillou,Jacob,Terrier,Goumont
scheme or table
p. 8891 - 8895
(2009/12/24)
Studies on Pyrazines. 29. High Regioselective Synthesis of Chloropyrazines from 3-Substituted Pyrazine 1-Oxides
Reaction of 3-methoxy- or 3-chloropyrazine 1-oxides with refluxing phosphoryl chloride in the presence of amine led to a high regioselective formation of 3-substituted 2-chloropyrazines.In contrast, the use of chloroacetyl chloride instead of phosphoryl chloride enabled different regioselectivity to yield 6-substituted 2-chloropyrazines, particularly 3-methoxycarbonylpyrazine 1-oxide was almost exclusively converted into methyl 6-chloropyrazinecarboxylate under conditions without the amine.
Sato, Nobuhiro,Fujii, Megumi
p. 1177 - 1180
(2007/10/02)
Studies on Pyrazines. Part 10. Substitution Effect on Reaction of Pyrazine N-Oxides with Phosphoryl chloride
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Sato, Nobuhiro
p. 2860 - 2875
(2007/10/02)
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