8-Hydroxy-1-naphthaldehyde reacts with hydrazine to give 1H-benzo[de]cinnoline; some reduction to 8-methyl-1-naphthol also takes place. The oxime of 8-hydroxy-1-naphthaldehyde does not cyclise analogously to an oxazine; instead dehydration to the nitrile occurs.
P. H. Lacy and D. C. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1975, 419 DOI: 10.1039/P19750000419
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