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Synthesis 1990; 1990(11): 1008-1010
DOI: 10.1055/s-1990-27078
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A Facile One-Pot Synthesis of 3,4-Dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine and Derivatives

Mogens Havsteen Jakobsen* , Ole Buchardt, Arne Holm, Morten Meldal
  • *Center for Medical Biotechnology, Chemical Laboratory II, The H. C. Ørsted Institute, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen, Denmark
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Publication Date:
17 September 2002 (online)

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A new one-pot synthesis of 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine (Dhbt-OH) and derivatives directly from anthranilic acids is described. The reaction of anthranilic acids and thionyl chloride affords unstable sulfinamide anhydrides which are treated with O-(trimethylsilyl)hydroxylamine followed by diazotization to give the corresponding Dhbt-OH derivatives in good overall yield.