Formation of 3-aryl-5-nitroisocoumarins from 5-nitroisocoumarins and aromatic acyl chlorides under Friedel-Crafts conditions.
Treatment of 5-nitroisocoumarin with aromatic acyl chlorides under Friedel-Crafts conditions gives 3-aryl-5-nitroisocoumarins, rather than the expected 4-acyl-5-nitroisocoumarins. This procedure was optimized for reaction temperature (150 degrees C), solvent (nitrobenzene), and Lewis acid (SnCl4). Reaction of 5-nitroisocoumarin with [13C]-carbonyl benzoyl chloride under the optimum conditions gave 5-nitro-3-phenylisocoumarin in which the 13C is located at the 3-C of the heterocycle, indicating that the benzoyl carbon framework is incorporated intact.
Sunderland
Peter T
PT
Department of Pharmacy & Pharmacology, University of Bath, Claverton Down, Bath, United Kingdom.
Thompson
Andrew S
AS
Threadgill
Michael D
MD
D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular
D003374:Coumarins; D009574:Nitro Compounds