Copper(I)-Catalyzed Intramolecular Tandem Acylation/O-Arylation under Mild Conditions: Synthesis of Benzofuro[3,2-c]quinolin-6(5H)-ones and G-Quadruplex-Targeting Analogues.

ABSTRACT: This paper presents a copper(I)-catalyzed intramolecular tandem acylation/O-arylation of methyl 2-[2-(2-bromophenyl)acetamido]benzoates for the synthesis of benzofuro[3,2-c]quinolin-6(5H)-ones under mild conditions. The combination of CuI, 1,10-phenanthroline, and K₂CO₃ in DMSO was found to be the optimal reaction condition, producing the target products in high yields (84-99%) at 70 °C for 16 h. The tandem reaction was applicable to substrates bearing halo, electron-withdrawing, and electron-donating groups at their phenyl moieties with a broad substrate scope. Further derivation produced compounds serving as G-quadruplex DNA (G4 DNA) stabilizers. The most potent analogue, 2,9-bis{[3-(diethylamino)propyl]amino}-5-methylbenzofuro[3,2-c]quin

SUBMITTER: Chiou SJ 

PROVIDER: S-EPMC11731314 | biostudies-literature | 2025 Jan

REPOSITORIES: biostudies-literature