Diastereoselective Synthesis of Functionalized 5‐Amino‐3,4‐Dihydro‐2 H ‐Pyrrole‐2‐Carboxylic Acid Esters: One‐Pot Approach Using Commercially Available Compounds and Benign Solvents

2021 ◽  
Author(s):  
Sara Meninno ◽  
Mario Carratù ◽  
Jacob Overgaard ◽  
Alessandra Lattanzi
Keyword(s):  
Carboxylic Acid ◽  
Diastereoselective Synthesis ◽  
One Pot ◽  
Benign Solvents ◽  
Acid Esters

Indol-2-Carboxylic Acid Esters Containing N-Phenylpiperazine Moiety - Preparation and Cholinesterase-inhibiting Activity

2020 ◽  
Vol 17 (7) ◽  
pp. 576-587
Author(s):  
Tereza Padrtová ◽  
Pavlína Marvanová ◽  
Renáta Kubínová ◽  
Jozef Csöllei ◽  
Oldřich Farsa ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Quaternary Ammonium ◽  
Quaternary Ammonium Salts ◽  
Biologically Active ◽  
Ammonium Salts ◽  
Inhibiting Activity ◽  
One Pot ◽  
Basic Part ◽  
The One ◽  
Acid Esters

Background: The indole derivatives and the N-phenylpiperazine fragment represent interesting molecular moieties suitable for the research of new potentially biologically active compounds. This study was undertaken to identify if indol-2-carboxylic acid esters containing N-phenylpiperazine moiety possess acetylcholinesterase and butyrylcholinesterase inhibitory activity. Materials and Methods: The study dealt with the synthesis of a novel series of analogs of 1H-indole-2- carboxylic acid and 3-methyl-1H-indole-2-carboxylic acid. The structure of the derivatives was represented by the indolylcarbonyloxyaminopropanol skeleton with the attached N-phenylpiperazine or diethylamine moiety, which formed a basic part of the molecule. The final products were synthesized as dihydrochloride salts, fumaric acid salts, and quaternary ammonium salts. The first step of the synthetic pathway led to the preparation of esters of 1H-indole-2-carboxylic acid from the commercially available 1H-indole-2-carboxylic acid. The Fischer indole synthesis was used to synthesize derivatives of 3-methyl-1H-indole-2-carboxylic acid. Results and Discussion: Final 18 indolylcarbonyloxyaminopropanols in the form of dihydrochlorides, fumarates, and quaternary ammonium salts were prepared using various optimization ways. The very efficient way for the formation of 3-methyl-1H-indole-2-carboxylate (Fischer indole cyclization product) was the one-pot synthesis of phenylhydrazine with methyl 2-oxobutanoate with acetic acid and sulphuric acid as catalysts. Conclusion: Most of the derivatives comprised of an attached N-phenylpiperazine group, which formed a basic part of the molecule and in which the phenyl ring was substituted in position C-2 or C-4. The synthesized compounds were subjected to cholinesterase-inhibiting activity evaluation, by modified Ellman method. Quaternary ammonium salt of 1H-indole-2-carboxylic acid which contain N-phenylpiperazine fragment with nitro group in position C-4 (7c) demonstrated the most potent activity against acetylcholinesterase.

One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acid esters and amidoximes using potassium carbonate

2006 ◽  
Vol 47 (22) ◽  
pp. 3629-3631 ◽  
Author(s):  
Kande K.D. Amarasinghe ◽  
Matthew B. Maier ◽  
Anil Srivastava ◽  
Jeffrey L. Gray
Keyword(s):  
Carboxylic Acid ◽  
Potassium Carbonate ◽  
One Pot ◽  
One Pot Synthesis ◽  
Acid Esters

One-Pot Synthesis of 1,2,4-Oxadiazoles from Carboxylic Acid Esters and Amidoximes Using Potassium Carbonate.

ChemInform ◽  
2006 ◽  
Vol 37 (36) ◽  
Author(s):  
Kande K. D. Amarasinghe ◽  
Matthew B. Maier ◽  
Anil Srivastava ◽  
Jeffrey L. Gray
Keyword(s):  
Carboxylic Acid ◽  
Potassium Carbonate ◽  
One Pot ◽  
One Pot Synthesis ◽  
Acid Esters

scholarly journals Organobase-catalyzed three-component reactions for the synthesis of 4H-2-aminopyrans, condensed pyrans and polysubstituted benzenes

2014 ◽  
Vol 10 ◽  
pp. 141-149 ◽  
Author(s):  
Moustafa Sherief Moustafa ◽  
Saleh Mohammed Al-Mousawi ◽  
Maghraby Ali Selim ◽  
Ahmed Mohamed Mosallam ◽  
Mohamed Hilmy Elnagdi
Keyword(s):  
Carboxylic Acid ◽  
Acid Ester ◽  
Synthetic Methods ◽  
Efficient Synthesis ◽  
One Pot ◽  
Carboxylic Acid Ester ◽  
Acid Esters

Novel routes for the preparation of 2-amino-4H-pyran-3-carbonitrile 9, amino-arylbenzoic acid ester derivatives 13a,b, 2-aminotetrahydro-4H-chromene-3-carbonitrile 18, 3-amino-4-cyanotetrahydronaphthalene-2-carboxylic acid ester 26 and 4-amino-3,5-dicyanophthalic acid ester derivatives 37a–c were developed. The synthetic methods utilize one-pot reactions of acetylene carboxylic acid esters, α,β-unsaturated nitriles and/or active methylenenitriles in the presence of L-proline or DABCO. Plausible mechanisms are suggested for the formation of the products. Finally, these compounds were used for the efficient synthesis of 6-amino-5-cyanonicotinic acid ester derivatives 31a,b, ethyl 4-amino-5H-pyrano[2,3-d]pyrimidine-6-carboxylates 33a,b, 4-amino-6H-pyrrolo[3,4-g]quinazoline-9-carbonitrile 39, and 1,7-diamino-6-(N'-hydroxycarbamimidoyl)-3-oxo-5-phenyl-3H-isoindole-4-carboxylate (40).

"One-Pot" Conversion of Carboxylic Acid Esters and Lactones to Olefinic Compounds

Synthesis ◽  
1980 ◽  
Vol 1980 (12) ◽  
pp. 1015-1017 ◽  
Author(s):  
Wilhelm Boland ◽  
Peter Ney ◽  
Lothar Jaenicke
Keyword(s):  
Carboxylic Acid ◽  
One Pot ◽  
Acid Esters

New One-Pot Preparation of α,β-Unsaturated Carboxylic Acid Esters from Carbonyl Compounds

Synthesis ◽  
1988 ◽  
Vol 1988 (07) ◽  
pp. 537-538 ◽  
Author(s):  
George A. Olah ◽  
An-hsiang Wu ◽  
Omar Farooq ◽  
G. K. Surya Prakash
Keyword(s):  
Carboxylic Acid ◽  
Carbonyl Compounds ◽  
One Pot ◽  
Unsaturated Carboxylic Acid ◽  
Acid Esters

The first one-pot ambient-temperature synthesis of 1,2,4-oxadiazoles from amidoximes and carboxylic acid esters

Tetrahedron ◽  
2017 ◽  
Vol 73 (7) ◽  
pp. 945-951 ◽  
Author(s):  
Sergey Baykov ◽  
Tatyana Sharonova ◽  
Anton Shetnev ◽  
Sergey Rozhkov ◽  
Stanislav Kalinin ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Ambient Temperature ◽  
Temperature Synthesis ◽  
One Pot ◽  
Acid Esters

scholarly journals Diastereoselective Synthesis of Spiro and Chlorocyclopropanes from Camphorpyrazolidinone derived -Unsaturated Amides

2020 ◽  
Author(s):  
sudershan gondi
Keyword(s):  
Carboxylic Acid ◽  
Asymmetric Synthesis ◽  
Diastereoselective Synthesis ◽  
Optically Pure ◽  
Acid Esters

<p>High diastereoselectivity are observed in the addition of gem-dichlorocarbene to an optically pure a,b-unsaturated amides derived from a chiral camphorpyrazolidinone. A novel route to the asymmetric synthesis of spiro [2,2]-pentane carboxylic acid esters derivatives<em> </em><em>through gem</em>-dichlorocyclopropane is described.</p>

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