Some heterocycles from dehydro-L-ascorbic acid and dehydro-D-isoascorbic acid

Department of Chemistry, Faculty of Science, Alexandria, Egypt Department of Physics and Chemistry, Faculty of Education, Damanhour, Alexandria University, Egypt Manuscript received 5 January 1999, revised 7 September 1999, accepted 13 September 1999 Reaction of D-erythro-2,3-hexodiulosono-1,4-lactone-2-phenylhydrazone 1 with p-sulfamylphenylhydrazine gives the 3-p­sulfamylphenylhydrazone 2, which upon treatment with hydrazine hydrate or CuCl2 affords pyrazolinedione 4 or 3,6-anhydro derivative 6, respectively. Condensation of the aldehyde 8 with thiosemicarbazide or hydroxylamine produces 3- carboxaldehydethiosemicarbazone 12 or hydroxyiminomethyl derivative 9, which reacts with BzCI to give the bicyclic 11. Reaction of the furotriazole 14 with hydrazine hydrate gives carboxylic acid hydrazide 15 which upon treatment with some carbonyl compounds or CS2 yields acylhydrazones 6-20, 22 or binuclear heterocycle 27. Acetylation of 2, 4 and 9 gives the corresponding acetylated derivatives 3, 5 and 10, while that of 12, 16, 19, 20 and 22 produces the corresponding cyclized derivatives 13, 23-26