Premium
Orthogonal Synthesis of Fluorinated Acridones and Acridines from Perfluorobenzophenone
Author(s) -
Del Buttero Paola,
Gironda Ramona,
Moret Massimo,
Papagni Antonio,
Parravicini Matteo,
Rizzato Silvia,
Miozzo Luciano
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001647
Subject(s) - chemistry , nucleophilic aromatic substitution , regioselectivity , nucleophilic substitution , electrophilic aromatic substitution , amine gas treating , radical nucleophilic aromatic substitution , nucleophile , solvent polarity , solvent , acridine derivatives , substitution reaction , base (topology) , catalysis , acridone , organic chemistry , stereochemistry , mathematical analysis , mathematics
The reaction between perfluorobenzophenone and aromatic amines proceeds with the substitution of one or more fluorine atoms. The regiochemistry of this substitution is controlled by solvent polarity, temperature, and nucleophilic character of the amine. o ‐Anilinononafluorobenzophenone can be selectively transformed into acridines or acridones by using acid or base catalysis through electrocyclization or aromatic nucleophilic substitution.