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Studies on pyrazines. Part 27. A new deoxidative nucleophilic substitution of pyrazine N-oxides; synthesis of azidopyrazines with trimethylsilyl azide
Abstract
Azidopyrazines bearing amino, methoxy and/or phenyl groups have been synthesized by reaction of pyrazine N-oxides with trimethylsilyl azide in the presence of diethylcarbamoyl chloride in refluxing acetonitrile. In most cases, the azidation occurs only at the carbon α to the N-oxide function, and 3-substituted pyrazine 1-oxides gave 2-azido-3-substituted pyrazines. Conversely, methyl, chloro and methoxycarbonylpyrazine N-oxides did not undergo azidation. The electronic and steric effects of the substituent on the reactivity are discussed.
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