The ortho-substituent on 2,4-bis(trifluoromethyl)phenylboronic acid catalyzed dehydrative condensation between carboxylic acids and amines

2018 ◽  
Vol 54 (43) ◽  
pp. 5410-5413 ◽  
Author(s):  
Ke Wang ◽  
Yanhui Lu ◽  
Kazuaki Ishihara
Keyword(s):  
Carboxylic Acids ◽  
Boron Atom ◽  
Boronic Acid ◽  
Phenylboronic Acid ◽  
Acid Catalyzed ◽  
Ortho Substituent

The ortho-substituent of boronic acid plays a key role in preventing the coordination of amines to the boron atom.

Boronic-Acid-Catalyzed Regioselective and 1,2-cis-Stereoselective Glycosylation of Unprotected Sugar Acceptors via SNi-Type Mechanism

2018 ◽  
Vol 140 (10) ◽  
pp. 3644-3651 ◽  
Author(s):  
Masamichi Tanaka ◽  
Akira Nakagawa ◽  
Nobuya Nishi ◽  
Kiyoko Iijima ◽  
Ryuichi Sawa ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Stereoselective Glycosylation ◽  
Acid Catalyzed

scholarly journals Adsorption and Release of Rose Bengal on Layer-by-Layer Films of Poly(Vinyl Alcohol) and Poly(Amidoamine) Dendrimers Bearing 4-Carboxyphenylboronic Acid

Polymers ◽  
2020 ◽  
Vol 12 (8) ◽  
pp. 1854 ◽  
Author(s):  
Kentaro Yoshida ◽  
Akane Yamaguchi ◽  
Hiroki Midorikawa ◽  
Toshio Kamijo ◽  
Tetsuya Ono ◽  
...  
Keyword(s):  
Rose Bengal ◽  
Boronic Acid ◽  
Vinyl Alcohol ◽  
Acidic Solution ◽  
Phenylboronic Acid ◽  
Poly Vinyl Alcohol ◽  
Basic Solution ◽  
Layer By Layer ◽  
Lbl Films ◽  
H2o2 Solution

Phenylboronic acid-bearing polyamidoamine dendrimer (PBA-PAMAM)/poly(vinyl alcohol) (PVA) multilayer films were prepared through the layer-by-layer (LbL) deposition of PBA-PAMAM solution and PVA solution. PBA-PAMAM/PVA films were constructed successfully through the formation of boronate ester bonds between the boronic acid moiety in PBA and 1,3-diol units in PVA. When the (PBA-PAMAM/PVA)5 films were immersed in rose bengal (RB) solution, RB was adsorbed onto the LbL films. The amount of RB adsorbed was higher in the LbL films immersed in acidic solution than in basic solution. The release of RB from the LbL films was also promoted in the basic solution, while it was suppressed in the acidic solution. The boronic acid ester is oxidized to phenol by hydrogen peroxide (H2O2) and the carbon-boron bond is cleaved, so that the (PBA-PAMAM/PVA)5 films can be decomposed by immersion in H2O2 solution. Therefore, when RB-adsorbed (PBA-PAMAM/PVA)5 films were immersed in H2O2 solution, the release of RB was moderately promoted when the solution was weakly acidic.

A new and practical boronic acid catalyzed intramolecular cyclodehydration of ureas for the synthesis of LFA-1 antagonists

2011 ◽  
Vol 52 (19) ◽  
pp. 2465-2467 ◽  
Author(s):  
Rogelio P. Frutos ◽  
Thomas Tampone ◽  
Jason A. Mulder ◽  
Yibo Xu ◽  
Diana Reeves ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Acid Catalyzed

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.

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