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RESEARCH PRODUCT
One-Pot Synthesis of Pyrrole-2-carboxylates and -carboxamides via an Electrocyclization/Oxidation Sequence
Till OpatzDennis ImbriNatalie NetzMurat KucukdisliLisa Marie KammerPhilipp JungAnnika Kretzschmannsubject
ProlineOrganic ChemistryOne-pot synthesischemistry.chemical_elementHalogenationEstersStereoisomerismStereoisomerismElectrochemistryRing (chemistry)Combinatorial chemistryCopperCatalysisCatalysischemistry.chemical_compoundchemistryCyclizationElectrochemistryPyrrolesOxidation-ReductionCopperPyrroledescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-10-29 | The Journal of Organic Chemistry |