Potential Nootropic Agents: Synthesis of Some 1,4-Disubstituted 2-Oxopyrrolidines and Some Related Compounds

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Title:Potential Nootropic Agents: Synthesis of Some 1,4-Disubstituted 2-Oxopyrrolidines and Some Related Compounds
Creators:
Valenta, Vladimír
Urban, Jiří
Taimr, Jan
Polívka, Zdeněk
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 5, pp. 1126-1136

Abstract

<p>4-(Aminomethyl)-1-benzyl-2-oxopyrrolidine (<i>VI</i>) was transformed by treatment with (4-benzhydrylpiperazin-1-yl)carbonyl chlorides <i>IIIb</i> - <i>IIId</i> and with (4-methylpiperazin-1-yl)carbonyl chloride (<i>IIIa</i>) to the carboxamides <i>IVa</i> - <i>IVd</i>. Heating of 1-(ethoxycarbonylmethyl)-2,4-dioxopyrrolidine (<i>XIX</i>) in acetonitrile in the presence of water afforded <i>XVIIIa</i>. Treatment with ammonia led to the diamide <i>XVIIIc</i>, while alkaline hydrolysis of <i>XVIIIa</i> gave the dicarboxylic acid <i>XVIIIb</i>. 4-(Aminomethyl)-1-(4-methylthiobenzyl)-2-oxopyrrolidine (<i>XII</i>) was prepared by the reaction of 4-(methylthio)benzylamine with itaconic acid and the following sequence of reactions starting from the obtained carboxylic acid <i>VII</i> including esterification, reduction and treatment the obtained alcohol <i>IX</i> with thionyl chloride, synthesis of phthalimido derivative <i>XI</i> and hydrazinolysis. Amine <i>XII</i> added to 4-chlorophenyl isocyanate formed <i>XIII</i>. The compounds prepared were tested for nootropic activity.

Title:Potential Nootropic Agents: Synthesis of Some 1,4-Disubstituted 2-Oxopyrrolidines and Some Related Compounds
Creators:
Valenta, Vladimír
Urban, Jiří
Taimr, Jan
Polívka, Zdeněk
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:59
Number:5
Page Range:pp. 1126-1136
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19941126UNSPECIFIED
ID Code:531
Item Type:Article
Deposited On:06 Feb 2009 17:01
Last Modified:06 Feb 2009 16:01

Citation

Valenta, Vladimír; Urban, Jiří; Taimr, Jan; Polívka, Zdeněk (1994) Potential Nootropic Agents: Synthesis of Some 1,4-Disubstituted 2-Oxopyrrolidines and Some Related Compounds. Collection of Czechoslovak Chemical Communications, 59 (5). pp. 1126-1136. ISSN 0010-0765

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