Synthesis and Applications of 4-Arylquinoline-2(1H)Ones and Bisquinolones via Microwave

Jamshed Hashim, Toma N. Glasnov and C. Oliver Kappe, Karl-Franzens-University Graz

Date Posted: Thursday, September 21, 2006

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Abstract

In recent years, increased interest in the synthesis of functionalized 4-arylquinolin-2(1H)-ones with promising bioligical properties has been observerd. A number of analogues of this class of heterocyclic structure have been reported as lead compounds or are undergoing clinical trials.

In addition, many natural products, pharmaceuticals, herbicides and fine chemicals contain symmetrical or unsymmetrical biaryl units. We have therefore focused our attention on the synthesis of both 4-arylquinolones of type A and bisquinolones of type B using transition metal-catalysed reactions assisted by microwave(MW) irradiation.

Biologically active 4-aryl-3-alkenyl-substituted quinolin-2(1H)-ones (A) and functionalised 4,4´-bisquinolones (B) can be synthesized by controlled MW irradiation.1

Key steps in the synthesis of compound A include the derivatization of the quinolin-2-(1H)-one cores using palladium catalysed Suzuki and Heck reactions, installing the 4-aryl and 3-alkenyl substituents. All synthetic transformations (six steps) are MW-assisted.

Functionalized 4,4´-isquinolones B can be efficiently synthesized by MW-assisted palladium(0)-catalysed one-pot borylation/Suzuki cross coupling reactions or via nickel(0)-mediated homocouplings of 4-chloroquinolin-2(1H)-one precursors.Both coupling methods are also applicable to other types of symmetrical biaryls.2

1) Glasnov, T. N.; Stadlbauer, W.; Kappe, C. O. J. Org. Chem. 2005, 70, 3864
2) Hashim, J.; Glasnov, T. N; Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2006, 71, 1707

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