Synthesis and further studies of chemical transformation of the 2-aryl-3-halogenoquinolin-4(1h)-one derivatives

Abstract

Specially prepared 2-arylquinolin-4(1H)-ones and their 2-aryl-1-methyl-4-quinolone derivatives were converted in high yield and purity to the corresponding C-3 brominated products using pyridinium tribromide in acetic acid at room temperature. The 2-arylquinolin-4(1H)-ones were reacted with iodine and Na2CO3 mixture in THF at room temperature to produce the 3-iodo-2-arylquinolin-4(1H)-one derivatives. The latter were, in turn, N-methylated using NaH-MeI mixture in dry THF to afford the corresponding 2-aryl-3-iodo-1-methyl-4-quinolone derivatives.

The 3-iodo-2-arylquinolin-4(1H)-one and 2-aryl-3-iodo-1-methyl-4-quinolones were converted to 2,3-diarylquinolin-4(1H)-one and 2,3-diaryl-1-methyl-4-quinolones following Suzuki cross-coupling reaction method, respectively.

The 2-aryl-3-bromoquinolin-4(1H)-ones, on the other hand, were converted to 2-aryl-3-bromo-4-chloroquinoline derivatives using phosphorus oxychloride under reflux. The 2-aryl-3-bromo-4-chloroquinoline were then transformed to the corresponding 2-aryl-3-bromo-4-N-(4'-chloroaryl)-4-aminoquinolines derivatives using 4-chloroaniline in ethanol under reflux. The products synthesized in this investigation were characterised using a combination of 1H NMR, 13C NMR, IR and mass spectroscopic techniques.