title: One-pot synthesis of tri- and tetrasubstituted pyridines by sequential ring-opening/cyclization/oxidation of N-arylmethyl 3-aziridinylpropiolate esters.
abstract: A novel strategy for the one-pot synthesis of substituted pyridines from N-arylmethyl 3-aziridinylpropiolate esters is described. The method employs a three-step procedure including the formation of allenyl imines, phosphine-catalyzed cyclization, and subsequent oxidation of the dihydropyridines. Depending on the reaction conditions of the final oxidation step, tri- and tetrasubstituted pyridines can be selectively produced.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505 (Japan). yoshi@tokushima-u.ac.jp.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Yoshida
authors.forename: Tomotaka
authors.initials: T
authors.lastname: Mizuguchi
authors.forename: Kosuke
authors.initials: K
authors.lastname: Namba
mesh_terms: D002384:Catalysis; D003500:Cyclization; D004952:Esters; D007097:Imines / Q000737:chemistry; D010084:Oxidation-Reduction; D010720:Phosphines / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004952:Esters; D007097:Imines; D010720:Phosphines; D011725:Pyridines; C044646:phosphine
keywords: cyclization; heterocycles; organocatalysis; small ring compounds; synthetic methods