Regioselective synthesis of substituted pyrroles: efficient palladium-catalyzed cyclization of internal alkynes and 2-amino-3-iodoacrylate derivatives.
The first efficient and regioselective palladium-catalyzed cyclization of internal alkynes and 2-amino-3-iodoacrylates to give moderate to excellent yields of highly functionalized pyrroles has been developed. This approach is applicable to a range of alkynes and affords the deacylated pyrrole under reaction conditions for most substrates. [reaction: see text]
Crawley
Matthew L
ML
Discovery Medicinal Chemistry and Discovery Analytical Chemistry, Wyeth Research, 500 Arcola Road, Collegeville, PA 19426, USA. crawlem@wyeth.com
Goljer
Igor
I
Jenkins
Douglas J
DJ
Mehlmann
John F
JF
Nogle
Lisa
L
Dooley
Rebecca
R
Mahaney
Paige E
PE
D000179:Acrylates / Q000138:chemical synthesis*; D000215:Acylation; D000480:Alkynes / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010165:Palladium / Q000737:chemistry*; D011188:Potassium / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis*
D000179:Acrylates; D000480:Alkynes; D002254:Carbonates; D011758:Pyrroles; D010165:Palladium; C037593:potassium carbonate; D011188:Potassium