[reaction: see text] Biologically active 4-aryl-3-alkenyl-substituted quinolin-2(1H)-ones have been synthesized in a short and concise manner employing readily available 4-hydroxyquinolin-2(1H)-ones as intermediates. Key steps in the synthesis include the derivatization of the quinolin-2(1H)-one cores using palladium-catalyzed Suzuki and Heck reactions, installing the 4-aryl and 3-alkenyl substituents. All synthetic transformations (six steps) required for the synthesis of the desired target quinolin-2(1H)-one were carried out using controlled microwave-assisted organic synthesis.

Highly fluorescent and stable 6,7-dimethoxy-2-oxoquinoline-4-carbonitriles (11) were synthesized starting from appropriate 4-hydroxyquinolones 3 via reactive 4-chloroquinolones 8 by using toluenesulfinates as catalysts. In contrast to the well-described 4-trifluoromethyl-substituted analogues 18, N-substituted derivatives 11 fluoresce in water, polar, and apolar solvents in a narrow 430-440-nm window with almost constant quantum yield of 0.5. Equal excitation is possible in the broad double maximum between 385 and 410 nm yield-

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The use of malonates such as diethyl malonates 9, (chlorocarbonyl)ketenes 15 and bis(2,4,6-trichlorophenyl) malonates 18 as reagents for cyclocondensation with 1,3-dinucleophiles to give six-membered heterocycles is described. Further attempts to use malonates such as bis(trimethylsilyl) malonates 19 and bis(carbamimidoyl) malonates 29 as new cyclocondensation agents are described .

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