title: One-pot synthesis of pyrrole-2-carboxylates and -carboxamides via an electrocyclization/oxidation sequence.
abstract: An electrocyclic ring closure is the key step of an efficient one-pot method for the synthesis of pyrrole-2-carboxylates and -carboxamides from chalcones and glycine esters or amides. The 3,4-dihydro-2H-pyrrole intermediates generated in situ are oxidized to the corresponding pyrroles by stoichiometric oxidants or by catalytic copper(II) and air in moderate to high yields. A wide range of functional groups are tolerated, and further combination with an in situ bromination gives access to polyfunctional pyrrole scaffolds.
authors.affiliation: Institute of Organic Chemistry, University of Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.
authors.forename: Dennis
authors.initials: D
authors.lastname: Imbri
authors.forename: Natalie
authors.initials: N
authors.lastname: Netz
authors.forename: Murat
authors.initials: M
authors.lastname: Kucukdisli
authors.forename: Lisa Marie
authors.initials: LM
authors.lastname: Kammer
authors.forename: Philipp
authors.initials: P
authors.lastname: Jung
authors.forename: Annika
authors.initials: A
authors.lastname: Kretzschmann
authors.forename: Till
authors.initials: T
authors.lastname: Opatz
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D004563:Electrochemistry; D004952:Esters; D010084:Oxidation-Reduction; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004952:Esters; D011758:Pyrroles; C002986:2-pyrrolecarboxylic acid; D003300:Copper; D011392:Proline