Sequential Brønsted acid promoted amination/annulation/aromatization of β-(2-aminophenyl)-α,β-ynones with cyclic α-methylene carbonyl compounds has been developed for the synthesis of polycyclic quinolines in good to high yields in ethanol. The protocol achieves the selective formation of the target quinolines and is expected to find practical applications due to its operational simplicity.
A divergent domino condensation/ biannulation reaction of β-(2-aminophenyl)-α,β-ynones with 1,3-dicarbonyls to construct the polycyclic 4H-pyrano[3,4-c]quinoline core has been developed. The p-TsOH·H2O catalyzed reaction of β-(2-aminophenyl)-α,β-ynones with β-ketoesters in ethanol proceeds...
The diversity-oriented synthesis of 2,2,3-substituted-2,3-dihydroquinolin-4(1H)-ones vs. functionalised quinoline or N-alkenylindole derivatives is described.
The palladium-catalyzed synthesis of indole/benzofuran-containing diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.
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