0000000000395293
AUTHOR
Annika Kretzschmann
One-Pot Synthesis of Pyrrole-2-carboxylates and -carboxamides via an Electrocyclization/Oxidation Sequence
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.
ChemInform Abstract: One-Pot Synthesis of Pyrrole-2-carboxylates and -carboxamides via an Electrocyclization/Oxidation Sequence.
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.
CCDC 1055316: Experimental Crystal Structure Determination
Related Article: Dennis Imbri , Natalie Netz , Murat Kucukdisli , Lisa Marie Kammer , Philipp Jung , Annika Kretzschmann , and Till Opatz|2014|J.Org.Chem.|79|11750|doi:10.1021/jo5021823
CCDC 1055315: Experimental Crystal Structure Determination
Related Article: Dennis Imbri , Natalie Netz , Murat Kucukdisli , Lisa Marie Kammer , Philipp Jung , Annika Kretzschmann , and Till Opatz|2014|J.Org.Chem.|79|11750|doi:10.1021/jo5021823