Heterocyclization Reactions of Isonitroso β-Diketones with Hydrazine Hydrate and Alkylhydrazines

Abstract

A previously unknown isonitroso diketone containing a naphthalen-1-yl substituent was synthesized. Its condensation with hydrazine hydrate resulted in the isolation for the first time of 3-(memoxymemyl)-5-(naphthalen-1-yl)-4-nitroso-1H-pyrazole. The cycloaromatization reaction of isonitroso β-diketones containing naphthalen-1-yl, phenyl, and methoxymethyl substituents with alkyl hydrazines was studied. The structure of the novel 4-methoxy-1-(naphthalen-1-yl)butan-1,2,3-trione 2-oxime, its condensation product with hydrazine hydrate, as well as N-alkyl-substituted 4-nitroso-1H-pyrazoles was confirmed by ¹H and ¹³C NMR, IR, and UV spectroscopy and mass spectrometry.