title: Copper-catalyzed Perkin-acyl-Mannich reaction of acetic anhydride with pyridine: expeditious entry to unconventional piperidines.
abstract: A regioselective introduction of a methoxycarbonyl methyl group at the C(2) position of unsubstituted pyridine has been accomplished with catalytic amounts of copper(II) triflate in mild reaction conditions. The N-acetyl-1,2-dihydropyridyl acetic acid methyl ester obtained is a valuable building block for the synthesis of new polyfunctionalized piperidine derivatives bearing unconventional substitution patterns.
authors: Dipartimento di Scienze Farmaceutiche, Sede di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy.
authors: Stefano
authors: S
authors: Crotti
authors: Francesco
authors: F
authors: Berti
authors: Mauro
authors: M
authors: Pineschi
mesh_terms: D000089:Acetic Anhydrides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000089:Acetic Anhydrides; D010880:Piperidines; D011725:Pyridines; C031800:acetic anhydride; D003300:Copper; C023666:pyridine