Novel solid-phase synthetic method for combinatorial generation of a 4-hydroxyquinolin-2(1H)-one-based library

Utilizing polymer-bound anthranilic acid derivatives, we were able to obtain 4-hydroxyquinolin-2(1H)-ones in 50-99% five- or six-step overall yields and 65-95% purities through the adaptation of a Dieckmann-type condensation reaction to a C-C bond-forming cyclative cleavage step. The reactions on solid phase were monitored by on-bead ATR-FTIR spectroscopic methods, colorimetric tests, and/or cleavage experiments.