title: Formation of 3-aryl-5-nitroisocoumarins from 5-nitroisocoumarins and aromatic acyl chlorides under Friedel-Crafts conditions.
abstract: 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.
authors: Department of Pharmacy & Pharmacology, University of Bath, Claverton Down, Bath, United Kingdom.
authors: Peter T
authors: PT
authors: Sunderland
authors: Andrew S
authors: AS
authors: Thompson
authors: Michael D
authors: MD
authors: Threadgill
mesh_terms: D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D003374:Coumarins; D009574:Nitro Compounds