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Synthesis of Amino-1,2,4-triazoles by Reductive ANRORC Rearrangements of 1,2,4-Oxadiazoles

  作者 PICCIONELLO ANTONIO PALUMBO; GUARCELLO ANNALISA; BUSCEMI SILVESTRE; VIVONA NICOLO; PACE ANDREA  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-24;  页码  8724-8727  
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[摘要]The reaction of various 1,2,4-oxadiazoles with an excess of hydrazine in DMF has been investigated. 3-Amino-1,2,4-triazoles are produced through a reductive ANRORC pathway consisting of the addition of hydrazine to the 1,2,4-oxadiazole followed by ring-opening, ring-closure, and final reduction of the 3-hydroxylamino-1,2,4-triazole intermediate. The general applicability of 1,2,4-oxadiazoles ANRORC reactivity is demonstrated also in the absence of C(5)-linked electron-withdrawing groups.

 
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