129574-31-8Relevant articles and documents
Sterically Hindered N-Aryl-2(1H)-Quinolones and N-Aryl-6(5H)-Phenanthridinones: Separation of Enantiomers and Barriers to Racemization
Mintas, Mhaden,Mihaljevic, Vesna,Koller, Helmut,Schuster, Doris,Mannschreck, Albrecht
, p. 619 - 624 (2007/10/02)
The novel N-aryl-4-chloro-3-methyl-2(1H)-quinolones (1)-(4) have been synthesized by condensation of the appropriate diphenylamine with diethyl methylmalonate and subsequent chlorination of the resulting N-aryl-4-hydroxy-3-methyl-2(1H)-quinolones (7)-(10). 5-(1-Naphthyl)-6(5H)-phenanthridinone (5) has been synthesized by the Chapman rearrangement of the 6-(1-naphthoxy)phenanthridine (11).Separation of the enantiomers (M) and (P) of the quinolones (1)-(4) and phenanthridinones (5), (6) was achieved by liquid chromatography on triacetylcellulose.The barriers to partial rotation about the C-N bond in (1)-(6) were determined by thermal racemization of enantiomers and are compared with those of structurally related molecules.