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Synthesis 1994; 1994(9): 931-934
DOI: 10.1055/s-1994-25607
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Studies on Pyrazines; Part 30:1 Synthesis of Aminopyrazines from Azidopyrazines

Nobuhiro Sato* , Tomoyuki Matsuura, Naoko Miwa
  • *Department of Chemistry, Yokohama City University, Yokohama 236, Japan
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Publication Date:
17 September 2002 (online)

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Azidopyrazines do not undergo reduction by reagents that are effective for the preparation of alkyl- or arylamines from the azides because the heterocyclic azides exist in the bicyclic form of tetrazolo[1,5-a]pyrazines. Nevertheless, the conversion into aminopyrazines was achieved by hydrogenolysis in the presence of ammonium hydroxide and palladium-on-carbon or particularly by reduction with tin(II) chloride in methanolic hydrochloric acid, in 34-87% yields. To elucidate the successful progress of the reaction, the equilibrium of azide-tetrazole was examined by 1H NMR spectroscopy in various solvents.