An efficient strategy for constructing C3–C4-disubstituted tetrahydroquinolines from quinolines via a sequential reductive dearomatization/regioselective nitration/enantioselective enal addition was developed.
8-Hydroxy-5-nitroquinoline is an antimicrobial, anti-inflammatory and anticancer agent. Our findings on its photochemistry reveal that it tautomerizes and dissociates in the excited state, suggesting the drug delivered should be protected from light.
Two total syntheses of quindoline were achieved. The PPh3-mediated generation of a key nitrene caused the unprecedented formation of a phosphazene. The reaction mechanism was studied by a DFT approach.
A versatile two-step environmentally friendly synthesis of imidazo[4,5,1-ij]quinolines is described.
This review summarizes modern stereoselective enolate and homoenolate Michael addition/annulation reactions to nitroalkene-containing benzo-fused heterocycles, enabling efficient access to complex polycyclic heterocycles with biological importances.