A Convenient Synthesis of 3-Amino-1,2,4-benzotriazine 1,4-Dioxide (SR 4233) and Related Compounds via Nucleophilic Aromatic Substitution Between Nitroarenes and Guanidine Base

Abstract

Reaction of 1-fluoro-2-nitrobenzene or 1,2-dinitrobenzene with guanidine in hot THF followed by treatment with potassium tert-butoxide gave 3-amino-1,2,4-benzotriazine 1-oxide in good yield, which was further oxidized by peracetic acid to afford the title compound.