Alkaline hydrolysis of the methyl esters of benzo[b]furan-2- and 3-, benzo[b]thiophen-2- and 3-, and indole-2- and 3-carboxylic acids

1969 ◽  
pp. 205 ◽  
Author(s):  
A. Feinstein ◽  
P. H. Gore ◽  
G. L. Reed
Keyword(s):  
Carboxylic Acids ◽  
Alkaline Hydrolysis ◽  
Methyl Esters ◽  
Hydrolysis Of

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.

Ribonucleosides of 3-amino- and 3,5-diaminopyrazole-4-carboxylic acid and their open-chain analogues: Synthesis and reactions

1986 ◽  
Vol 51 (7) ◽  
pp. 1512-1531 ◽  
Author(s):  
Maria K. Spassova ◽  
Antonín Holý ◽  
Milena Masojídková
Keyword(s):  
Carboxylic Acid ◽  
Acid Hydrolysis ◽  
Carboxylic Acids ◽  
Sodium Salt ◽  
Alkaline Hydrolysis ◽  
Trimethylsilyl Derivative ◽  
Open Chain ◽  
Silyl Derivatives ◽  
Hydrolysis Of

Bis(trimethylsilyl) derivative of ethyl 3-aminopyrazole-4-carboxylate (VI) and tris(trimethylsilyl) derivative of ethyl 3,5-diaminopyrazole-4-carboxylate (VII) on reaction with 2,3,5-tri-O-benzoyl-D-ribofuranolyl chloride and subsequent debenzoylation afforded the respective β-D-ribofuranosyl derivatives VIIIa and Xa. Their alkaline hydrolysis led to 1-(β-D-ribofuranosyl)-3-aminopyrazole-4-carboxylic acid (VIIIc) and 1-(β-D-ribofuranosyl)-3,5-diaminopyrazole-4-carboxylic acid (Xb). The esters VIIIa and Xa were not ammonolyzed under normal conditions. Contrary to nucleosidation of the silyl derivatives VI and VII, sodium salt of ethyl 3-aminopyrazole-4-carboxylate was alkylated with 4-chloromethyl-2,2-dimethyl-1,3-dioxolane (XI) or 5-(p-toluenesulfonyloxy)-1,3-dioxane (XVIIb) to give a mixture of the N-isomeric derivatives XIIIa, XIXa and XIIa, XVIIIa, respectively; sodium salt of the 3,5-diamino derivative V reacted with these synthons under formation of the corresponding compounds XIIIb and XXa. Subsequent alkaline and acid hydrolysis of XIIa and XIIIb gave the open-chain analogs of nucleosides XV and XVI. The N-(1,3-dioxan-5-yl) derivatives XVIIIc and XXa resisted acid hydrolysis, giving rise only to carboxylic acids XVIIIb and XXb.

Synthesis and properties of 5-styryl-2-furancarboxylic acids

1981 ◽  
Vol 46 (11) ◽  
pp. 2724-2728 ◽  
Author(s):  
Viera Knoppová ◽  
Anton Beňo ◽  
Jaroslav Kováč
Keyword(s):  
Ir Spectra ◽  
Transmission Coefficient ◽  
Alkaline Hydrolysis ◽  
Methyl Esters ◽  
Uv And Ir Spectra ◽  
Substituted Benzaldehydes ◽  
Hydrolysis Of

5-(4-X-Styryl)-2-furancarboxylic acids (X = H, Br, NO2, COOCH3, (CH3)2N) were prepared by oxidation of the appropriate 5-(4-X-styryl)-2-furaldehydes, or alternatively by alkaline hydrolysis of the corresponding methyl esters. The latter were obtained by reacting the 4-substituted benzaldehydes with 5-methoxycarbonylfuryltriphenylphosphonium chloride. The UV and IR spectra of products are commented. The apparent pK values of the synthesized acids were employed for calculation of the transmission coefficient π' through the benzene-furan system bridged by a -CH=CH- group.

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