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Copper‐Catalyzed One‐Pot Tandem Reaction for the Synthesis of Imidazo[1,2‐ c ][1,2,3]triazolo[1,5‐ a ]quinazolines
Author(s) -
Nandwaitesh K.,
Shinde Vikki N.,
Saini Hitesh K.,
Kumar Anil
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701221
Subject(s) - chemistry , cycloaddition , sodium azide , catalysis , alkyne , intramolecular force , combinatorial chemistry , copper , tandem , medicinal chemistry , ligand (biochemistry) , cascade reaction , annulation , coupling reaction , click chemistry , stereochemistry , organic chemistry , biochemistry , materials science , receptor , composite material
A copper‐catalyzed tandem reaction of 2‐(2‐bromoaryl)imidazoles/2‐(2‐bromoaryl)benzimidazoles, alkynes, and sodium azide was developed for the synthesis of imidazo[1,2‐ c ][1,2,3]triazolo[1,5‐ a ]quinazolines in moderate to excellent yields (50–85 %). The one‐pot method involves copper‐catalyzed azide–alkyne cycloaddition (CuAAC), intramolecular cross‐dehydrogenative C–N bond formation, and Ullmann‐type C–N coupling. This protocol involves the use of air as the oxidant under mild and ligand‐free reaction conditions, and the reaction can be performed with a broad range of substrates with high efficiency.