78161-64-5Relevant academic research and scientific papers
p-Methyl-N-(pentafluorobenzylidene)aniline (1), 1,2,3,4-Tetrafluoro-7-methoxyacridine (2), 1,2,3,4,7-Pentafluoroacridine (3) and 2-(p-Methylanilino)-1,3,4-trifluoro-7-methylacridine (4): Four Molecules Representing Key Stages in the One-Pot Synthesis of 1
Adamson, A. J.,Archambeau, Y.,Banks, R. E.,Beagley, B.,Helliwell, M.,et al.
, p. 967 - 971 (1994)
All of the title compounds, C14H8F5N, C14H7F4NO, C13H4F5N and C21H15F3N2, display a characteistic stacking of their ? systems in which adjacent members of the stack are related by crystallographic inversion centres.This leads to a particularly efficient m
One-pot synthesis of 1,2,3,4-tetrafluoroacridines from pentafluorobenzaldehyde
Adamson, Adrian J.,Banks, R. Eric,Fields, Roy,Tipping, Anthony E.
, p. 530 - 555 (2007/10/03)
Treatment of pentafluorobenzaldehyde with a two-molar equivalence of aniline in o-dichlorobenzene at ca. 180 yields a complex mixture of products from which 1,2,3,4-tetrafluoroacridine (1a) and its 3-anilino derivative (7a) can be isolated in at least 48
A new one-pot synthesis of 1,2,3,4-tetrafluoroacridines and some 7-substituted derivatives
Adamson, Adrian J.,Banks, Ronald E.,Tipping, Anthony E.
, p. 5 - 10 (2007/10/02)
1,2,3,4-Tetrafluoroacridine (1a) and a range of 7-substituted analogues can be synthesised by heating pre-formed Schiff bases (E)-C6F5CH=NC6H4R-p (3) (from C6F5CHO + H2NC6H4R-p) with the parent aniline H2NC6H4R-p (1:1 molar ratio) or by heating a mixture of the aldehyde C6F5CHO and the aniline H2NC6H4R-p (R=H, OMe, Me, But, F, Cl and Br) (1:2 molar ratio) in toluene or 1,2-dichlorobenzene under reflux.The mechanism has been deduced through the isolation in certain reactions of ortho-substituted Schiff bases 2-(p-RC6H4NH)C6F4CH=NC6H4R-p (6) (R=Cl or Br), which on acid catalysis (by p-RC6H4NH3(+)F(-)) undergo ring-closure with elimination of the aniline p-RC6H4NH2.Except where R=F, Cl or Br, substantial amounts of the corresponding 3-anilino-1,2,4-trifluoroacridines 5 are also formed; these arise via sequential para- and ortho-substitution of fluorine in the pentafluorophenyl moiety of the Schiff bases.The synthesis is capable of extension to other fluorinated aromatic aldehydes, e.g. the formation of 1-fluoro-7-methoxyacridine (9) from 2,6-difluorobenzaldehyde and p-anisidine.
