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2,6‐Bis(amido)benzoic Acid with Internal Hydrogen Bond as Brønsted Acid Catalyst for Friedel–Crafts Reaction of Indoles
Author(s) -
Moriyama Katsuhiko,
Sugiue Toru,
Saito Yuki,
Katsuta Shoichi,
Togo Hideo
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201401189
Subject(s) - chemistry , benzoic acid , friedel–crafts reaction , moiety , catalysis , amide , brønsted–lowry acid–base theory , hydrogen bond , adduct , medicinal chemistry , organic chemistry , carboxylic acid , titration , molecule
Benzoic acid catalysts bearing two amide groups that increase the Brønsted acidity of the carboxylic acid moiety by internal hydrogen‐bonding interactions were designed as a novel class of carboxylic acid catalysts for the Friedel–Crafts reaction of indoles with β‐nitrostyrenes and 3,3‐disubstituted 3 H ‐indoles to obtain the corresponding Friedel–Crafts adducts in high yields. The internal hydrogen‐bonding benzoic acid catalysts have a relatively high Brønsted acidity compared with benzoic acid based on the p K a measurements in DMSO by UV spectrophotometric titration.
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