A versatile cyclodehydration reaction for the synthesis of isoquinoline and beta-carboline derivatives.
The direct conversion of various amides to isoquinoline and beta-carboline derivatives via mild electrophilic amide activation, with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine, is described. Low-temperature amide activation followed by cyclodehydration upon warming provides the desired products with short overall reaction times. The successful use of nonactivated and halogenated phenethylene derived amides, N-vinyl amides, and optically active substrates is noteworthy.
Movassaghi
Mohammad
M
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA. movassag@mit.edu
Hill
Matthew D
MD
D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D002243:Carbolines; D007546:Isoquinolines; C039109:isoquinoline