title: Combinatorial synthesis of nicotine analogs using an Ugi 4-CR/cyclization-reduction strategy.
abstract: A practical one-pot synthesis of nicotine analogs from Ugi 4-CR/propargyl adducts is reported. This methodology allows the rapid construction of the pyrrolidine moiety present in nicotine through an intramolecular base-promoted 5-endo cycloisomerization process, followed by a reduction of the resulting mixture of 2- and 3-pyrrolines to afford nicotine analogs in good overall yields.
authors.affiliation: Departamento de Química Orgánica, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510, México, D.F., Mexico. joseavm@unam.mx.
authors.forename: Luis A
authors.initials: LA
authors.lastname: Polindara-García
authors.forename: Alfredo
authors.initials: A
authors.lastname: Vazquez
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003500:Cyclization; D062425:Hydroxybenzoate Ethers / Q000737:chemistry; D015394:Molecular Structure; D009538:Nicotine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D010293:Pargyline / Q000031:analogs & derivatives / Q000737:chemistry; D011437:Propylamines / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D062425:Hydroxybenzoate Ethers; D011437:Propylamines; D011725:Pyridines; C009054:propargylamine; C051439:pyridinecarboxaldehyde; D010165:Palladium; D009538:Nicotine; D010293:Pargyline