1171753-50-6Relevant articles and documents
A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating
Santos, Gabriela F.D.,Anjos, Nicolas S.,Gibeli, Miguel M.,Silva, Guilherme A.,Fernandes, Pamela C.S.,Fiorentino, Everton S.C.,Longo, Luiz S.
, p. 1434 - 1444 (2020/10/14)
Over the last twenty years, the Groebke-Blackburn-Bienaymé (GBB) reaction has been emerged as a powerful tool to access different nitrogen-based heterocycles as privileged scaffolds in medicinal chemistry. This multicomponent reaction is usually catalyzed by ordinary Br?nsted or Lewis acid catalysts. Herein, we present a comparative study on the catalytic efficiencies of different rare earth triflates in GBB reactions under microwave heating, involving 2-aminopyridine or 2-aminothiazole, as aminoazole component, and different aldehydes and aliphatic isocyanides. The use of gadolinium(III) triflate as cheaper alternative catalyst for the most commonly used scandium(III) triflate was acknowledged for the first time, and a library of twenty three imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles could be obtained in good to excellent yields.
Three novel sequential reactions for the facile synthesis of a library of bisheterocycles possessing the 3-aminoimidazo[1,2- a ]pyridine core catalyzed by bismuth(III) chloride
Shahrisa, Aziz,Esmati, Somayeh
, p. 595 - 602 (2013/04/10)
Novel, one-pot, two-step, sequential protocols for the synthesis of 1,4-phenylene bisheterocyclic compounds have been developed. Successive sequencing of the Groebke-Blackburn-Bienaymé reaction with Ugi-azide, Hantzsch and Biginelli reactions results in rapid and efficient formation of bisheterocyclic compounds. A simple, fast and high yielding method for the synthesis of 3-aminoimidazo[1,2-a]pyridines catalyzed by bismuth(III) chloride under solvent-free conditions is reported. Bismuth(III) chloride is also an efficient catalyst for the Ugi-azide reaction under solvent free conditions. Georg Thieme Verlag Stuttgart - New York.
