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

1994 ◽  
Vol 59 (5) ◽  
pp. 1126-1136 ◽  
Author(s):  
Vladimír Valenta ◽  
Jiří Urban ◽  
Jan Taimr ◽  
Zdeněk Polívka
Keyword(s):  
Carboxylic Acid ◽  
Dicarboxylic Acid ◽  
Itaconic Acid ◽  
Thionyl Chloride ◽  
Alkaline Hydrolysis ◽  
Nootropic Activity ◽  
Carbonyl Chloride ◽  
Nootropic Agents ◽  
Hydrolysis Of ◽  
Related Compounds

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

Isocarbostyrils. II. The Conversion of 2-Methyl-4-acyl-5-nitroisocarbostyrils to 2-Substituted Indole-4-carboxylic Acids

1971 ◽  
Vol 49 (17) ◽  
pp. 2797-2802 ◽  
Author(s):  
D. E. Horning ◽  
G. Lacasse ◽  
J. M. Muchowski
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Alkaline Hydrolysis ◽  
Mannich Reaction ◽  
Reductive Cyclization ◽  
Acid Catalyzed ◽  
Acid Anhydrides ◽  
Hydrolysis Of ◽  
Derivatives Of

The sulfuric acid catalyzed acylation of 2-methyl-5-nitroisocarbostyril with carboxylic acid anhydrides gave the corresponding 4-acylated derivatives 3, which underwent reductive cyclization to 2-substituted derivatives of 4-methyl-1,3,4,5-tetrahydropyrrolo[4.3.2.de]isoquinolin-5-one (4). Alkaline hydrolysis of the six-membered lactam in 4 was accompanied by a retro-Mannich reaction to produce 2-substituted indole-4-carboxylic acids in about 40 % overall yield from 3.

Synthesis of 5-Phenylcytosine Nucleoside Derivatives

1996 ◽  
Vol 61 (4) ◽  
pp. 645-655 ◽  
Author(s):  
Marcela Krečmerová ◽  
Hubert Hřebabecký ◽  
Antonín Holý
Keyword(s):  
Acetic Anhydride ◽  
Thionyl Chloride ◽  
Alkaline Hydrolysis ◽  
Hydrogen Bromide ◽  
Analogous Reaction ◽  
Final Reaction Product ◽  
Cyclic Sulfite ◽  
Higher Temperature ◽  
Hydrolysis Of ◽  
Tin Tetrachloride

Reaction of silylated 5-phenylcytosine with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribose, catalyzed with tin tetrachloride, and subsequent methanolysis afforded 5-phenylcytidine (2). This compound reacted with thionyl chloride in acetonitrile to give cyclic sulfite 3 which on heating in dimethylformamide was converted into 2,2'-anhydro-1-(β-D-arabinofuranosyl)-5-phenylcytosine (4). Analogous reaction of compound 2 with thionyl chloride at reflux gave 5'-chloro-5'-deoxy-2',3'-cyclic sulfite 5. Its heating in dimethylformamide afforded 5'-chloro-2,2'-anhydro derivative 6, mild alkaline hydrolysis led to 5'-chloro-5'-deoxy-5-phenylcytidine (7). Alkaline hydrolysis of 5-phenyl-2,2'-anhydrocytidine (4) gave 5-phenylcytosine arabinoside 8, whereas the 2,2'-anhydro derivative 6 afforded 1-(5-chloro-5-deoxy-β-D-arabinofuranosyl)-5-phenylcytosine (11). At higher temperature, the final reaction product was 2,5'-anhydro-5-phenylcytidine (12). 5'-Chloro-5'-deoxynucleosides 7 and 11 reacted with tri-n-butyl- stannane to give 5'-deoxyribofuranosyl and 5'-deoxyarabinofuranosyl derivatives 15 and 16. 5-Phenylcytidine (2) was converted into the N4-acetate 17 with acetic anhydride. Further reaction with acetic anhydride and hydrogen bromide in acetic acid afforded a mixture of peracetylated 2'-bromo and 3'-bromo derivatives 18 and 19. Reaction with Zn/Cu couple gave 5'-O-acetyl-5-phenyl-2',3'-didehydro derivative 20 and 2',3',5'-tri-O-acetyl-5-phenylcytidine (21). Compound 20 was deblocked to 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-phenylcytosine (22). Catalytic hydrogenation of compound 20 over palladium and subsequent deblocking of the protected 2',3'-dideoxy derivative 23 gave 1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-5-phenylcytosine (24).

Studies on the BAL2 mechanism for ester hydrolysis

1993 ◽  
Vol 71 (11) ◽  
pp. 1841-1844 ◽  
Author(s):  
Judy E. Douglas ◽  
Grant Campbell ◽  
Donald C. Wigfield
Keyword(s):  
Spectral Analysis ◽  
Carboxylic Acid ◽  
Alkaline Hydrolysis ◽  
Ester Hydrolysis ◽  
Mass Spectral Analysis ◽  
Mass Spectral ◽  
Hydrolysis Of

The preparation and alkaline hydrolysis of 18O-methyl 2,2-dimethylpropanoate and 18O-methyl triphenylacetate are reported. From mass spectral analysis of the carboxylic acid products, it is concluded that the former substrate is hydrolyzed exclusively by the BAC2 mechanism, whereas the latter substrate proceeds 95% by the BAC2 mechanism and 5% by the BAL2 mechanism. The balance between these two mechanisms is discussed.

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