14146-78-2Relevant articles and documents
Tricarbonylmethane Acylhydrazones: Reactions under Acylating Conditions and Formation of Fused Isoxazole Derivatives with Concomitant N-N Bond Cleavage
Somogyi, Laszlo,Sohar, Pal
, p. 1903 - 1906 (2007/10/03)
Reactivity of 3-(1-acylhydrazonoethyl)-2H-pyran-2-ones 1a-k and 4a-d towards various acetylating agents and nitrous acid, respectively, is studied.Treatment of dehydroacetic acid (DHA) (thio)acylhydrazones 1a, c, f with Ac2O/Et3N afforded the 3-(1-triacetylhydrazinoethenyl) derivative 3a.The analogous coumarin derivative 5 was obtained by treatment of acetylhydrazone 4a with AcCl/PhNMe2.With concomitant N-N bond cleavage acylhydrazones 1c-f were converted to the pyrano-isoxazole 6 by treatment with NaNO2/AcOH whereas coumarin derivative 4d was converted to the imine 4e. - Keywords: Hydrazones / Coumarins / Dehydroacetic acid (DHA) / Isoxazoles