Solid-phase traceless synthesis of selected nitrogen-containing heterocyclic compounds. The Encore technique for directed sorting of modular solid support

The acid lability of electron-rich N-benzylanilines has been exploited in a linker for the traceless solid-phase synthesis of benzimidazoles, 2-aminob enzimidazoles, quinoxalinones and tetrahydroquinoxalines. The target compou nd precursors were assembled on a solid-phase support derivatized with eith er a benzylamine or a benzhydrylamine linker. Exposure to an acidic reagent caused cleavage of the C(benzyl)-N(aniline) bond, releasing the product wi th only a hydrogen atom on the descending nitrogen. The Encore technique fo r directed sorting on SynPhase Lanterns has been developed and applied to c ombinatorial synthesis of generic drug discovery libraries.