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Paper | Special issue | Vol 37, No. 1, 1994, pp.379-386
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S18
Aminations with Oxaziridines – Synthesis of Aryl- and Hetarylhydrazines

Siegfried Andreae* and Ernst Schmitz

*Zentrum für Selektive Organisch Synthese, KAI e V., Rudower Chaussee 5, D-12489, Berlin-Adlershof, Germany


Five acetylaminobenzenes (2) (X=CH), two 3-acetylaminopyridines (2) (X=N) and one 3-acetylaminopyridine-1-oxide (2) (X=N(O)) are aminated by 1-oxa-2-azaspiro[2.5]octane (1) / DABCO to cyclohexylidenehydrazino compounds (3), which are characterized as benzaldehyde or 4-nitrobenzaldehydehydrazones (4). In some cases the acetyl group is removed during the amination.