Superacid-promoted reactions of alpha-ketoamides and related systems.
The superacid-promoted reactions of alpha-hydroxy and alpha-ketoamides have been studied. Ionization of these compounds leads to varied aryl-substituted oxyindole products. In some cases, electrocyclization can lead to substituted fluorene products. Dicationic, superelectrophilic intermediates are proposed as intermediates leading to the products from alpha-hydroxy and alpha-ketoamides.
Sai
Kiran Kumar Solingapuram
KK
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA.
Esteves
Pierre M
PM
da Penha
Eduardo Tanoue
ET
Klumpp
Douglas A
DA
D000577:Amides / Q000737:chemistry*; D001561:Benzilates / Q000737:chemistry; D002412:Cations; D003500:Cyclization; D004563:Electrochemistry; D005449:Fluorenes / Q000737:chemistry; D006900:Hydroxylation; D007211:Indoles / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008333:Mandelic Acids / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D001561:Benzilates; D002412:Cations; D005449:Fluorenes; D007211:Indoles; D007659:Ketones; D008333:Mandelic Acids; C041509:fluorene; C037938:mandelic acid