V. Valenta et al., POTENTIAL NOOTROPIC AGENTS - SYNTHESIS OF SOME 1,4-DISUBSTITUTED 2-OXOPYRROLIDINES AND SOME RELATED-COMPOUNDS, Collection of Czechoslovak Chemical Communications, 59(5), 1994, pp. 1126-1136
4-(Aminomethyl)-1-benzyl-2-oxopyrrolidine (VI) was transformed by trea
tment with (4-benzhydrylpiperazin-1-yl)carbonyl chlorides IIIb - IIId
and with (4-methylpiperazin-1-yl)carbonyl chloride (IIIa) to the carbo
xamides IVa - IVd. Heating of 1-(ethoxycarbonylmethyl)-2,4-dioxopyrrol
idine (XIX) in acetonitrile in the presence of water afforded XVIIIa.
Treatment with ammonia led to the diamide XVIIIc, while alkaline hydro
lysis of XVIIIa gave the dicarboxylic acid XVIIIb. inomethyl)-1-(4-met
hylthiobenzyl)-2-oxopyrrolidine (XII) was prepared by the reaction of
4-(methylthio)benzylamine with itaconic acid and the following sequenc
e of reactions starting from the obtained carboxylic acid VII includin
g esterification, reduction and treatment the obtained alcohol IX with
thionyl chloride, synthesis of phthalimido derivative XI and hydrazin
olysis. Amine XII added to 4-chlorophenyl isocyanate formed XIII. The
compounds prepared were tested for nootropic activity.