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Sodium 4‐amino‐5‐hydroxy‐7‐sulfonaphthalene‐2‐sulfonate an efficient ligand for click reaction in water: Synthesis of 1,2,3‐triazole pharmacophore linked‐quinazolinone scaffold
Author(s) -
Keivanloo Ali,
Bakherad Mohammad,
Mokhtarei Lotfollah
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3832
Subject(s) - chemistry , pharmacophore , quinazolinone , ligand (biochemistry) , sulfonate , triazole , amide , carboxylate , combinatorial chemistry , 1,2,3 triazole , click chemistry , salt (chemistry) , propargyl , organic chemistry , medicinal chemistry , sodium , catalysis , stereochemistry , receptor , biochemistry
Water soluble sodium 4‐amino‐5‐hydroxy‐7‐sulfonaphthalene‐2‐sulfonate ligand was used successfully for the preparation of 1,2,3‐triazoles pharmacophore linked‐quinazolinone scaffold. The reaction of ethyl 4‐oxo‐3,4‐dihydroquinazoline‐2‐carboxylate and related amide compounds with propargyl bromide afforded ethyl 4‐oxo‐3‐(prop‐2‐yn‐1‐yl)‐3,4‐dihydroquinazoline‐2‐carboxylate and its amide derivatives. The reaction of propargylated compounds with azides catalyzed by copper (II) salt, in the presence of Sodium 4‐amino‐5‐hydroxy‐7‐sulfonaphthalene‐2‐sulfonate as a ligand in water produced novel 1,2,3‐triazole pharmacophore linked‐quinazolinone‐4‐one scaffold with high‐to‐excellent yields. The ligand assisted in the click reaction and reduced loading of copper salt to 2 mol%. Simplicity, short reaction times, use of water as green solvent, and low catalyst loading are the main advantages of this procedure.