title: Solid-phase synthesis of imidazo[4,5-b]pyridin-2-ones and related urea derivatives by cyclative cleavage of a carbamate linkage.
abstract: A solid-phase synthesis of substituted cyclic urea derivatives as potential heterocyclic library scaffolds is described. 2-Amino-3-nitropyridine is attached to Wang resin via a carbamate linkage. Reduction of the nitro group was achieved with SnCl(2).2H(2)O. Reductive alkylation with a range of substituted benzaldehydes followed by cyclative cleavage afforded a small library of 3-substituted imidazo[4,5-b]pyridine-2-ones in 33-45% yield and 59-88% purity. Subsequently, this methodology was applied to the synthesis of 3-substituted imidazo[4,5-f]quinolin-2-ones.
authors.affiliation: Department of Chemistry, University of Liverpool, P.O. Box 147, Liverpool L69 3BX, UK. monika.ermann@evotecoai.com
authors.forename: Monika
authors.initials: M
authors.lastname: Ermann
authors.forename: Nadja M
authors.initials: NM
authors.lastname: Simkovsky
authors.forename: Stanley M
authors.initials: SM
authors.lastname: Roberts
authors.forename: David M
authors.initials: DM
authors.lastname: Parry
authors.forename: Andy D
authors.initials: AD
authors.lastname: Baxter