Radical migration of substituents of aryl groups on quinazolinones derived from N-acyl cyanamides.
A newly designed radical cascade involving N-acyl cyanamides is reported. It builds on aromatic homolytic substitutions as intermediate events and leads to complex heteroaromatic structures via an unprecedented radical migration of a substituent on aryl groups of quinazolinones (hydrogen or alkyl). Mechanistic considerations are detailed, which allowed us to devise fine control over the domino processes. The latter could be predictably stopped at several stages, depending on the reaction conditions. Finally, a surgical introduction of a trifluoromethyl substituent on a quinazolinone was achieved via the reported migration.
Larraufie
Marie-Hélène
MH
UPMC Univ Paris 06, Institut Parisien de Chimie Moleculaire (UMR CNRS 7201), C. 229, 4 Place Jussieu, 75005 Paris, France.
Courillon
Christine
C
Ollivier
Cyril
C
Lacôte
Emmanuel
E
Malacria
Max
M
Fensterbank
Louis
L
D001688:Biological Products / Q000138:chemical synthesis; D003484:Cyanamide / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry; D015394:Molecular Structure; D052999:Quinazolinones / Q000737:chemistry*
D001688:Biological Products; D005609:Free Radicals; D006841:Hydrocarbons, Aromatic; D052999:Quinazolinones; D003484:Cyanamide