Collect. Czech. Chem. Commun.
2001, 66, 1078-1106
https://doi.org/10.1135/cccc20011078
Solid-Phase Traceless Synthesis of Selected Nitrogen-Containing Heterocyclic Compounds. The Encore Technique for Directed Sorting of Modular Solid Support
Viktor Krchňák*, Jennifer Smith and Josef Vágner
SIDDCO, Inc., 9040 South Rita Rd., Tucson, AZ 85747, U.S.A.
Abstract
The acid lability of electron-rich N-benzylanilines has been exploited in a linker for the traceless solid-phase synthesis of benzimidazoles, 2-aminobenzimidazoles, quinoxalinones and tetrahydroquinoxalines. The target compound precursors were assembled on a solid-phase support derivatized with either a benzylamine or a benzhydrylamine linker. Exposure to an acidic reagent caused cleavage of the C(benzyl)-N(aniline) bond, releasing the product with only a hydrogen atom on the descending nitrogen. The Encore technique for directed sorting on SynPhase Lanterns has been developed and applied to combinatorial synthesis of generic drug discovery libraries.
Keywords: Heterocycles; Solid-phase synthesis; Combinatorial libraries; Benzimidazoles; Quinoxalines; Benzylamine linkers.
References: 55 live references.
