Modification of reaction rates by complex formation. V. Alkaline hydrolysis of some xanthine complexes of acetoxycinnamic acids and related compounds

1970 ◽  
Vol 92 (4) ◽  
pp. 863-866 ◽  
Author(s):  
Honore. Stelmach ◽  
Kenneth A. Connors
Keyword(s):  
Complex Formation ◽  
Alkaline Hydrolysis ◽  
Reaction Rates ◽  
Hydrolysis Of ◽  
Related Compounds

Substitutent Effects in Non-Aromatic Nitrogen Heterocycles: Alkaline Hydrolysis of Methyl N-Methyl (oxo)dihydropyridinecarboxylates and Diaza Analogues

1985 ◽  
Vol 38 (4) ◽  
pp. 637 ◽  
Author(s):  
LW Deady
Keyword(s):  
Alkaline Hydrolysis ◽  
Nitrogen Heterocycles ◽  
Reaction Rates ◽  
Ester Hydrolysis ◽  
Pyrimidine Derivatives ◽  
Polyfunctional Compounds ◽  
Hydrolysis Of ◽  
Derivatives Of

Ester hydrolysis studies on some isomeric methoxycarbonyl derivatives of N-methylpyridin-2- and 4-ones show that reaction rates are affected by the relative positions of CO2Me, =O and NMe functions in ways which could not be predicted. However, from limited result for analogous pyrimidine derivatives, it seems that reactivity in these polyfunctional compounds can be predicted from the pyridine data by assuming additivity of effects.

Potential antipsychotic agents: 2-Chloro- and 2-methyl-11-(2-piperazinoethoxy)-6,11-dihydrodibenzo[b,e]thiepins and some related compounds; Synthesis and pharmacology

1984 ◽  
Vol 49 (11) ◽  
pp. 2520-2530 ◽  
Author(s):  
Václav Bártl ◽  
Karel Šindelář ◽  
Vladimír Valenta ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
...  
Keyword(s):  
Sulfuric Acid ◽  
Alkaline Hydrolysis ◽  
Antipsychotic Agents ◽  
Similar Reaction ◽  
Substitution Reactions ◽  
Single Product ◽  
Hydrolysis Of ◽  
Related Compounds ◽  
Hydroxyethyl Piperazine ◽  
Neuroleptic Activity

Reactions of 2-chloro- and 2-methyl-6,11-dihydrodibenzo[b,e]thiepin-11-ol with 2-bromoethanol in the presence of sulfuric acid in boiling benzene afforded the 2-bromoethyl ethers VIa and VIb which were transformed by substitution reactions with 1-methylpiperazine, 1-(2-hydroxyethyl)-piperazine and 1-(ethoxycarbonyl)piperazine to the title compounds. Alkaline hydrolysis of the carbamate IVa gave the secondary amine IIIa. Treatment of the bromo ether VIa with 4-(4-chloro-3-trifluoromethylphenyl)piperidin-4-ol resulted in the piperidine derivative VIIa. Substitution reaction of 11-chloro-6,11-dihydrodibenzo[b,e]thiepin with 1-(2-methoxyethyl)piperazine and 1-(2-ethoxyethyl)piperazine led to the amino ethers VIII and IX. Reaction of 11-chloro-11-phenyl-6,11-dihydrodibenzo[b,e]thiepin with 2-dimethylaminoethanethiol in dimethylformamide at 90°C gave a mixture of two isomeric bases which was separated to the expected sulfide X and the base XII, resulting evidently after the rearrangement of the primary carbocation. A similar reaction of 3-dimethylaminopropanethiol afforded a single product of structure XI. Out of the compounds prepared, the ether VIII was found most interesting: it is little toxic and has significant antireserpine activity in two tests (is considered a potential antidepressant). The ethers Iab, Iab, IIIa and VIIa did not reveal the expected neuroleptic activity.

STUDIES ON RDX AND RELATED COMPOUNDS: VI. THE HOMOGENEOUS HYDROLYSIS OF CYCLOTRIMETHYLENETRINITRAMINE (RDX) AND CYCLOTETRAMETHYLENETETRANITRAMINE (HMX) IN AQUEOUS ACETONE, AND ITS APPLICATION TO ANALYSIS OF HMX IN RDX(B)

1951 ◽  
Vol 29 (9) ◽  
pp. 731-733 ◽  
Author(s):  
S. Epstein ◽  
C. A. Winkler
Keyword(s):  
Reaction Time ◽  
Alkaline Hydrolysis ◽  
Activation Energies ◽  
Aqueous Acetone ◽  
Second Order ◽  
Alkali Concentration ◽  
Calibration Curves ◽  
Hydrolysis Of ◽  
Related Compounds ◽  
Homogeneous Hydrolysis

Measurements of the rates of alkaline hydrolysis of cyclotrimethylenetrinitramine (RDX) and cyclotetramethylenetetranitramine (HMX) in aqueous acetone show these two reactions to involve consecutive steps, the first of which is second order and rate controlling. Activation energies were estimated as 14 and 25 kcal. respectively. By establishing calibration curves, and controlling temperature, alkali concentration relative to concentration of explosive, and reaction time, the differential hydrolysis permits analysis of the HMX content of RDX(B) with an error of approximately ±0.2% HMX.

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.

THE EFFECT ON REACTION RATES CAUSED BY THE SUBSTITUTION OF C14 FOR C12: I. THE ALKALINE HYDROLYSIS OF CARBOXYL-LABELED ETHYL BENZOATE

1949 ◽  
Vol 27b (10) ◽  
pp. 807-812 ◽  
Author(s):  
William H. Stevens ◽  
Richard W. Attree
Keyword(s):  
Alkaline Hydrolysis ◽  
Rate Constants ◽  
Room Temperature ◽  
Reaction Rates ◽  
Ethyl Benzoate ◽  
Hydrolysis Rate ◽  
Rate Of Hydrolysis ◽  
Hydrolysis Of

A study of the alkaline hydrolysis of C14 carboxyl-labeled ethyl benzoate has shown that the substitution of C14 for C12 changes the rate of hydrolysis of the ester. Ester molecules containing C14 hydrolyze at a slower rate than normal ester molecules. The ratio of the hydrolysis rate constants at room temperature has been found to be 0.86 ± 0.016.

Synthesis of 9-(2-phosphonylmethoxyethyl)adenine and related compounds

1987 ◽  
Vol 52 (11) ◽  
pp. 2801-2809 ◽  
Author(s):  
Antonín Holý ◽  
Ivan Rosenberg
Keyword(s):  
Methyl Ester ◽  
Ethyl Ester ◽  
Sodium Salt ◽  
Alkaline Hydrolysis ◽  
Inorganic Phosphate ◽  
Sodium Hydride ◽  
Analogous Reaction ◽  
Hydrolysis Of ◽  
Related Compounds

Diethyl 2-hydroxyethoxymethanephosphonate (VIII) was converted into diethyl 2-halogenoethoxymethanephosphonates IXa and IXb by reaction with triphenylphosphine and tetrachloromethane or tetrabromomethane; analogous reaction of VIII with p-toluenesulfonyl chloride afforded diethyl 2-(p-toluenesulfonyloxy)ethoxymethanephosphonate (IXc). Reaction of sodium salt of adenine with compounds IX led to 9-(2-diethoxyphosphonylmethoxyethyl)adenine (X). Compound X was converted into 9-(2-phosphonylmethoxyethyl)adenine (II) by treatment with bromotrimethylsilane whereas alkaline hydrolysis of X gave ethyl ester Vb. Reaction of 9-(2-hydroxyethyl)adenine (IIIa) or its N6-benzoyl derivative IIIb with dimethyl p-toluenesulfonyloxymethanephosphonate (IV) in the presence of sodium hydride, followed by alkaline hydrolysis yielded methyl ester Va. Morpholide XI reacted with an inorganic phosphate and diphosphate to give 9-(2-phosphorylphosphonylmethoxyethyl)adenine (XII) and 2-(diphosphorylphosphonylmethoxyethyl)adenine (XIII), respectively.

Influence of medium on alkaline hydrolysis of succinic acid monomethyl and monopropyl esters

1980 ◽  
Vol 45 (11) ◽  
pp. 2873-2882
Author(s):  
Vladislav Holba ◽  
Ján Benko
Keyword(s):  
Succinic Acid ◽  
Kinetic Parameters ◽  
Alkaline Hydrolysis ◽  
Specific Interactions ◽  
Nonaqueous Media ◽  
The Media ◽  
Kinetics Of ◽  
Hydrolysis Of

The kinetics of alkaline hydrolysis of succinic acid monomethyl and monopropyl esters were studied in mixed aqueous-nonaqueous media at various temperatures and ionic strengths. The results of measurements are discussed in terms of electrostatic and specific interactions between the reactants and other components of the reaction mixture. The kinetic parameters in the media under study are related to the influence of the cosolvent on the solvation sphere of the reactants.

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