Metal-free synthesis of 3,3-disubstituted oxoindoles by iodine(III)-catalyzed bromocarbocyclizations.
"I" did it: An iodine(III)-mediated bromocarbocyclization was elaborated as an efficient tool for the synthesis of oxoindoles. This method is applicable to a variety of structurally different substrates, also with chemically sensitive groups, and gives access to the heterocycles in a regio- and stereoselective fashion. The indole-2-ones obtained can be converted easily into structurally complex target compounds, such as the alkaloid physostigmine.
Institute of Organic Chemistry, RWTH Aachen, Aachen, Germany.
David C
DC
Fabry
Maciej
M
Stodulski
Stefanie
S
Hoerner
Tanja
T
Gulder
D000178:Acrylamides / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D001974:Bromosuccinimide / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D054879:Halogenation; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D010830:Physostigmine / Q000138:chemical synthesis*; D017680:Potassium Compounds / Q000737:chemistry
D000178:Acrylamides; D001965:Bromides; D007211:Indoles; D017680:Potassium Compounds; D010830:Physostigmine; C045985:methacrylamide; D001974:Bromosuccinimide; C039004:potassium bromide