title: Versatile access to C-4-substituted 2-amino-1,3-azoles from hydropyridines in oxidative conditions.
abstract: [Chemical reaction: see text] Various substituted 2-aminotetrahydroazolopyridines and 2-aminohexahydroazolopyridines have been prepared by bromine-mediated addition of protected guanidine or urea to hydropyridine derivatives. The pH-dependent regioselective cleavage of the resulting aminal function led to the 2-aminoazole products III. The yields of the bicycles of type II, and their conversion into azoles III depends on the electronic properties of the substituents on the nitrogen of the tetrahydopyridine.
authors.affiliation: Institut de Chimie des Substances Naturelles du CNRS, BP 1, Yvette, France.
authors.forename: Maria del Rayo Sanchez
authors.initials: Mdel R
authors.lastname: Salvatori
authors.forename: Robert
authors.initials: R
authors.lastname: Abou-Jneid
authors.forename: Saïd
authors.initials: S
authors.lastname: Ghoulami
authors.forename: Marie-Thérèse
authors.initials: MT
authors.lastname: Martin
authors.forename: Anne
authors.initials: A
authors.lastname: Zaparucha
authors.forename: Ali
authors.initials: A
authors.lastname: Al-Mourabit
mesh_terms: D000588:Amines / Q000737:chemistry*; D001393:Azoles / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011725:Pyridines / Q000737:chemistry*
chemical_list: D000588:Amines; D001393:Azoles; D011725:Pyridines