A. Srivastava et al., PREPARATION AND CHARACTERIZATION BY H-1-NMR SPECTROSCOPY OF SOME SUCCINHYDRAZIDE DERIVATIVES, Polish Journal of Chemistry, 68(1), 1994, pp. 29-35
An unusual six membered cyclic succinhydrazide is formed by the reacti
on of Diels-Alder adduct of athracene-maleic anhydride with hydrazine
hydrate in glacial acetic medium. Enolic form (7-a) has been character
ized in the solid as well as in solution. Similar products have been o
btained with phenylhydrazine (9-a), 2:4 dinitrophenylhydrazine (10) an
d 2-furoic acid hydrazide(11). With acetic anhydride (7-a) is transfor
med into N',N'-diacetyl succinimide system (12) indicating a high stab
ility of a five membered ring. On acetylation (9) and (10) yield N-ace
tyl (13) and O-acetyl (14) derivatives respectively, whereas (11) is t
ransformed into (12). The six membered succinhydrazide structure has b
een further supported by 1,2-cycloaddition of an azo group to an inden
e with the formation of a diazacyclobutane derivative (17).