A microwave assisted intramolecular-furan-Diels-Alder approach to 4-substituted indoles.
The key steps of a versatile new protocol for the convergent synthesis of 3,4-disubstituted indoles are the addition of an alpha-lithiated alkylaminofuran to a carbonyl compound, a microwave-accelerated intramolecular Diels-Alder cycloaddition and an in situ double aromatization reaction.
Petronijevic
Filip
F
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania, 15260, USA.
Timmons
Cody
C
Cuzzupe
Anthony
A
Wipf
Peter
P
D003500:Cyclization; D004583:Electrons; D005663:Furans / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis* / Q000528:radiation effects; D008094:Lithium / Q000737:chemistry; D008872:Microwaves
D005663:Furans; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D007211:Indoles; D008094:Lithium