Abstract
The amination of 3-amino- and 3-azidoindazoles by hydroxylamine-O-sulfonic acid in an alkaline medium yields previously unreported 1,3-diamino- and 1-amino-3-azidoindazoles. These products undergo slow autoxidation in chloroform solution to give 4-aminobenzo-1,2,3-triazine. The action of formic or acetic acid on 3-amino-1-benzylideneaminoindazole leads to recyclization and formation of 3-amino-2-benzylindazole, which is also formed in the catalytic hydrogenation of 1-benzylamino-3-nitro- and 1-benzylideneamino-3-nitroindazoles.
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Dyablo, O.V., Pozharskii, A.F., Kuz'menko, V.V. et al. Synthesis and Oxidation of 1,3-Diamino- and 1-Amino-3-azidoindazoles. Chemistry of Heterocyclic Compounds 37, 567–573 (2001). https://doi.org/10.1023/A:1011600420626
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DOI: https://doi.org/10.1023/A:1011600420626