title: Efficient synthesis of conformationally constrained, amino-triazoloazepinone-containing di- and tripeptides via a one-pot Ugi-Huisgen tandem reaction.
abstract: Herein we describe a catalyst-free procedure employing an Ugi-4CR between a β-azido-α-amino acid, propargylamine, an isocyanide and an aldehyde, followed by a thermal azide-alkyne Huisgen cycloaddition to generate a 16-member library of amino-triazoloazepinone-bearing di- and tripeptides with up to four points of diversification and high atom economy.
authors.affiliation: Research Group of Organic Chemistry, Departments of Chemistry and Bioengineering Sciences, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium. mouhamad.jida@vub.ac.be sballet@vub.ac.be.
authors.forename: T M A
authors.initials: TM
authors.lastname: Barlow
authors.forename: M
authors.initials: M
authors.lastname: Jida
authors.forename: D
authors.initials: D
authors.lastname: Tourwé
authors.forename: S
authors.initials: S
authors.lastname: Ballet
mesh_terms: D001381:Azepines / Q000737:chemistry*; D061565:Cycloaddition Reaction; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D019151:Peptide Library; D057786:Peptidomimetics / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*
chemical_list: D001381:Azepines; D004151:Dipeptides; D009842:Oligopeptides; D019151:Peptide Library; D057786:Peptidomimetics; D014230:Triazoles