Reaction of Dehydro-D-Erythorbic acid with a molar equivalent of Methyl-O-Phenylenediamine and Arylhydrazines

ABSTRACT

The arylhydrazono of 3-[D-erythro-2,3,4,Trihydroxy-l-oxobutyl]-methylquinoxalinones 2-4 were prepared, through, the condensation of the oxo-compound 1 [obtained by reacting dehydro-D-erythorbic acid with 4-methyl-l,2-phenylenediamine] with arylhydrazines. Periodate oxidation of 2 gave 3- [1-[Phenylhydrazono]-glyoxal-l-yl]-methylquinoxelinune 5, identical to that obtained from the L-threo-isomer, whereas boiling acetic anhydride causes the elimination of two molecules of water to afford a product identified as 3-[5-acetoxymethyl]-1-phenylpyrazol-3-y1-methylquinoxalinone 12, similar to that obtained from the phenyl analog. Methylation of these arylhydrazono derivatives with dimethyl sulfate afforded the corresponding N-methyl derivatives 6-8, which on periodate oxidation afforded the aldehyde 9, which gave the corresponding mixed bis-hydrazones. Action of alkali, causes the loss of one molecule of water from the arylhydrazono derivatives to afford the corresponding flevazoles 14 and 15, which on periodate oxidation afforded 1-aryl-3-formyl methylflavazoles 16 and 17, which condensed with benzoylhydrazine to give the corresponding hydrazones 18 and 19. Cyclisation of 18 and 19 using boiling acetic anhydride afforded the oxadiazoline derivatives 22 and 23, whereas action of iodine and mercuric oxide afforded the corresponding oxadiazoles 20 and 21