Z. M. El-Shafei

Acylated osazones and anhydro-derivatives

Abstract The phenylosazone acetates from pentoses, 6-deoxyhexoses and hexoses were boiled with acetic anhydride yielding dianhydrophenylosazone acetates of the type (Ia–c). Similarly, p -chlorophenylosazones from d -glucose, l -sorbose and d -arabinose yielded dianhydro- p -chlorophenylosazone acetates. Acetyl chloride reacted with the phenylosazones from d -glucose and d -galactose yielding the N -acetyl-tetra- O -acetyl derivatives (III) and (IV). The phenylosazones from d -glucose and l -sorbose gave a tetra- and a mono- O -benzoyl derivative, respectively, in crystalline form when an insufficient amount of benzoyl chloride was used during benzoylation.

Homologs of dehydro-l-ascorbic acid phenylosazone

Abstract The reaction of d -arabino-2,3-heptodiulosono-1,4-lactone (1) with phenylhydrazine gives two crystalline products, namely, a red bis(hydrazone) (2a), which was oxidized to bicyclic compound 4a, and a yellow pyrazoline (3a) which gave an anhydride (5a) on treatment with methanolic sulfuric acid. On similar treatment, d -erythro-2,3-hexodiulosono-1,4-lactone (6a) afforded a pyrazoline (7a). Esters of the compounds prepared are described.

Acylated saccharide hydrazones and osazones

Abstract Acetylation of D -galactose phenyl- and ( p -chlorophenyl)-hydrazone with boiling acetic anhydride, or with acetyl chloride in pyridine, afforded N -acetyl- O -acetyl derivatives, whereas with the ( p -nitrophenyl)hydrazone, only the O -acetyl derivative was obtained. Benzoyl chloride, being a stronger acylating agent, caused the N -benzoylation of D -galactose ( p -nitrophenyl)hydrazone, and, with hydrazone penta-acetates, gave the N -benzoylated O -acetylated derivatives. Some new acylhydrazones were prepared, but, because of their enolization, they failed to undergo the formazan reaction, and their acetates could not be converted into azoethylene derivatives.

Derivatives of osotriazoles and 4-formyl-2-phenyl-1,2,3-triazole

The benzylidene derivatives of D-xylose, D-arabinose, D-glucose, D-galactose, and L-sorbose phenylosotriazoles have been prepared in crystalline form. The pentose derivatives possessed one benzylidene residue, probably in the 4,5-positions, and the hexose derivatives possessed two benzylidene residues.

Reactions of benzil mono- and bis-arylhydrazones

A number of benzil and anisil mono- and bis-arylhydrazones were prepared. The behaviour of the monohydrazones indicated their existence in a chelated form (I). The bisarylhydrazones were acetylated and also cyclised to 2,4,5-triaryl-1,2,3-triazoles (III), whose bromination was studied. The u.v. and i.r. absorption data of the compounds prepared are given.