Synthesis of Dihydro- and Tetrahydro-1,2,4,5-tetrazines from the Reaction of Nitrilimines with 1-Substituted-1-methylhydrazine

Abstract

The reaction of nitrilimines (2) with 1-substituted-1-methylhydrazines (3–6) led to the formation of the respective amidrazones (7) when R = CH₃, Ph, and to the acyclic adducts (8,9) when R = CHO and COCH₃. The acyclic adducts underwent thermal oxidative cyclization at CH₃ to give the unexpected 1,2,4,5-tetrazines (10,11). Dihydro-l,2,4,5-tetrazines (12) were also seperated when R = CHO.

Keywords:

• Nitrilimines
• Hydrazines
• 1,2,4,5-tetrazines
• Amidrazones

Acknowledgment

The authors wish to thank Dr. W. Schrader, Max-Planck Institut fuer Kohlenforschung, Muelheirn, Germany, for obtaining the mass spectra.