Versatile access to C-4-substituted 2-amino-1,3-azoles from hydropyridines in oxidative conditions.
[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.
Salvatori
Maria del Rayo Sanchez
Mdel R
Institut de Chimie des Substances Naturelles du CNRS, BP 1, Yvette, France.
Abou-Jneid
Robert
R
Ghoulami
Saïd
S
Martin
Marie-Thérèse
MT
Zaparucha
Anne
A
Al-Mourabit
Ali
A
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*
D000588:Amines; D001393:Azoles; D011725:Pyridines