Solid-phase combinatorial synthesis of 4-hydroxyquinolin-2(1H)-ones

Article abstract of DOI:10.1016/S0040-4039(98)01320-3

Cyanoacetic acid was loaded on Wang resin and C-acylated using acid anhydrides and triethylamine as base. Resin cleavage with concomitant decarboxylation produces β-keto nitriles. In the case of isatoic anhydrides, the resin-bound acylated intermediates undergo cyclative cleavage upon heating, leading to 4hydroxyquinolin-2(1H)-ones.