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Synthesis 1997; 1997(8): 855-857
DOI: 10.1055/s-1997-1283
short paper
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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

Hitomi Suzuki* , Takehiko Kawakami
  • *Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-01, Japan, Fax +81(75)7512085; E-mail: suzuki@kuchem.kyoto-u.ac.jp
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Publication Date:
31 December 2000 (online)

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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.

1,2,4-benzotriazine 1-oxide and 1,4-dioxide - guanidine - nitroarenes - nucleophilic aromatic substitution