RESUMEN
The 4-aminoquinoline moiety is widely present in various bioactive compounds and marketed drugs, while the preparation of this target structure relies heavily on the amination of 4-chloroquinolines. Herein, an atom and step economic procedure was developed based on an aerobic dehydrogenative aromatization strategy. Unlike the well-known palladium-catalyzed dehydrogenative aromatization of cyclohexanones with amines, synergistic Pd/Cu catalysis is crucial for 2,3-dihydroquinolin-4(1H)-one type of substrates. Under the optimized conditions, a range of aromatic/aliphatic amines and 2,3-dihydroquinolin-4(1H)-ones were coupled to give the corresponding 4-aminoquinoline products in moderate to high yields, and the application of the current methodology for the preparation and late-stage diversification of marketed drugs was also demonstrated.
RESUMEN
Herein, a protecting-group-free protocol was developed to realize a time and step economy diversification of the Meridianin alkaloid. A broad range of substituents are tolerated to deliver the products in moderate to high yields, and the first synthesis of Meridianin B was achieved. The simplicity of this protocol enables the rapid construction of a Meridianin derivative library for antibiofilm evaluation. Preliminary results reveal that Meridianin derivatives were capable of inhibiting the Acinetobacter baumannii biofilm and lowering the antibiotic MIC synergistically.
