Sequential functionalisation of 2-aryl-4-chloro-3-iodoquinolines via palladium-catalysed cross-coupling with phenylboronic acid followed by displacement of the 4-chloro atom from the resulting 2,3-diaryl-4-chloroquinolines with methoxide ion yielded 2,3-diaryl-4-methoxyquinolines. The latter were also prepared via Suzuki-Miyaura crosscoupling of 2-aryl-3-iodo-4-methoxyquinolines with phenylboronic acid. Demethylation of the methoxy compounds (BBr 3 ) gave the 2,3-diaryl-4(1H)-quinolinones.

Staudinger reaction of the 2-aryl-4-azido-3-bromoquinolines and 2-aryl-4-azido-3-iodoquinolines with triphenyl phosphine in refluxing tetrahydrofuran afforded series of 2-aryl-3-halogeno-4-(triphenylphosphoranylideneamino)quinolines. The latter were, in turn, hydrolyzed to the corresponding primary 4-amino-2-aryl-3-(bromo/iodo)quinolines using 80% acetic acid under reflux. Tetrakis(triphenylphosphine)-palladium(0)-catalyzed Suzuki reaction of the 2-aryl-3-iodo-4-(triphenylphosphoranylideneamino)-quinolines with phenylboronic acid in dimethyl formamide in the presence of 2 M K 2 CO 3 followed by hydrolysis of the incipient 2,3-diaryl-4-(triphenylphosphoranylideneamino)quinolines with 80% acetic acid afforded the 4-amino-2,3-diarylquinolines.

Quinoline derivatives R 0410 2-Aryl-4-chloro-3-iodoquinolines (II) as Substrates for the Synthesis of 2,3-Diaryl-4-methoxyquinolines (VI). -(MPHAHLELE*, M. J.; MTSHEMLA, V.; J. Chem. Res. 2008, 8, 437-440; Dep. Chem., Coll. Sci. Eng. Technol., Univ. S. Afr., Pretoria 0003, S. Afr.; Eng.) -H. Toeppel 05-153

Quinoline derivatives R 0410 2-Aryl-4-azido-3-(bromo/iodo)quinolines as Substrates for the Synthesis of Primary 4-Amino-2,3-disubstituted QuinolineDerivatives. -The Staudinger reaction products (IV) are convenient precursors for the preparation of amines (V) and (VIII). -(MPHAHLELE*, M. J.; MTSHEMLA, V.; J. Heterocycl. Chem. 45 (2008) 5, 1343-1350; Dep. Chem., Coll. Sci. Eng. Technol., Univ. S. Afr., Pretoria 0003, S. Afr.; Eng.) -R. Staver 05-152