Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters via C–N bond activation

2018 ◽  
Vol 16 (17) ◽  
pp. 3099-3103 ◽  
Author(s):  
Weijie Yu ◽  
Shuwu Yang ◽  
Fei Xiong ◽  
Tianxiang Fan ◽  
Yan Feng ◽  
...  
Keyword(s):  
Quaternary Ammonium ◽  
Bond Activation ◽  
Bond Cleavage ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Carbonylation Reaction ◽  
Palladium Catalyzed ◽  
First Time ◽  
Acid Esters

An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C–N bond cleavage.

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.

ChemInform Abstract: SYNTHESIS OF QUATERNARY AMMONIUM SALTS BASED ON β-MORPHOLINOPROPIONIC ACID ESTERS

1978 ◽  
Vol 9 (41) ◽  
Author(s):  
S. I. AKCHURINA ◽  
G. P. KRUPNOV ◽  
A. P. BOGDANOV ◽  
F. S. SULEIMANOVA
Keyword(s):  
Quaternary Ammonium ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Acid Esters

Poly(arylene ether sulfone) crosslinked networks with pillar[5]arene units grafted by multiple long-chain quaternary ammonium salts for anion exchange membranes

2020 ◽  
Vol 56 (6) ◽  
pp. 928-931 ◽  
Author(s):  
Jinwu Peng ◽  
Minhui Liang ◽  
Zhenchao Liu ◽  
Peng Wang ◽  
Chengying Shi ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Anion Exchange ◽  
Quaternary Ammonium ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Anion Exchange Membranes ◽  
Arylene Ether ◽  
Crosslinked Networks ◽  
First Time ◽  
Long Chain

For the first time, high-molecular-weight pillar[5]arene-containing aromatic polymers were synthesized and further modified for application as anion exchange membranes.

Chemical transformations of quaternary ammonium salts via C–N bond cleavage

2020 ◽  
Vol 18 (6) ◽  
pp. 1057-1072 ◽  
Author(s):  
Zhong-Xia Wang ◽  
Bo Yang
Keyword(s):  
Quaternary Ammonium ◽  
Bond Cleavage ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Chemical Transformations

The reaction of quaternary ammonium salts via C–N bond cleavage to construct C–C, C–H and C–heteroatom bonds is summarized.

ChemInform Abstract: BACTERICIDAL QUATERNARY AMMONIUM SALTS BASED ON MONOCHLOROACETIC ACID ESTERS

1980 ◽  
Vol 11 (40) ◽  
Author(s):  
A. E. EPSHTEIN ◽  
V. E. LIMANOV ◽  
M. YU. TELEGIN ◽  
E. K. SKVORTSOVA ◽  
T. I. MAXSIMOVA
Keyword(s):  
Quaternary Ammonium ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Monochloroacetic Acid ◽  
Acid Esters
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