Reaction of N-Nitro-benzotriazole with Nucleophiles

Abstract

N-Nitro-benzotriazole 1 reacts with various C-nucleophiles 2 in tetrahydrofuran at room temperature to afford o-nitramidophenylazo-compounds 3a–f and o-nitramidophenyl hydrazones 3g–l, respectively. Reaction of 1 with sodium azide in aqueous acetonitrile gives a reactive 2-azidophenylnitramide intermediate 4 which is trapped by Cu-catalyzed 1,3-dipolar cycloadition with phenyl acetylene to afford 1-o-nitramidophenyl-4-phenyl-1,2,3-triazole 5. Reaction of 1 with trimethylsilylcyanide affords 3-amino-benzo[e][1,2,4]triazine 6.

Keywords:

• Azo compounds
• benzotriazole
• hydrazones
• ring opening
• tetrazine

ACKNOWLEDGMENTS

The authors thank K.-P. Zeller and G. Nicholson for performing the mass spectra and K. Albert for performing the NMR spectra. This work is financially supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.