A synthesis of 4H-1,3,4-benzoxadiazines [(V) and (VI)] from N-aroyl-N′-acetyl-N′-(2,4-dihalogenophenyl)-hydrazines is described. The process involves displacement of ortho-halogen, fluorine being more readily displaced than bromine; in some cases a smooth deacetylation [(V)→(VI)] follows ring closure. A synthesis of a 7-nitro-4H-1,3.4-benzoxadiazine from a hydrazonyl bromide is reported.
A. J. Elliott and M. S. Gibson, J. Chem. Soc., Perkin Trans. 1, 1972, 2915 DOI: 10.1039/P19720002915
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