Cyclisation of 2-amino-or 2-acetamido-2'-methoxybenzophenones occurred in the presence of sodium hydride to give 9-acridones. This is a method of wide applicability for the synthesis of substituted acridones. A mechanism Department of Chemistry, University of Aberdeen AB9 2U E, Scotland for the cyclisation is discussed.IN connection with studies on the synthesis of natural products under biomimetic conditions we became interested in the synthesis of naturally occurring 9-acridones, a group of alkaloids found only in the plant family Rutaceae.2 The similarity in ring number, ring size, and substituent pattern of the acridone alkaloids to xanthones 3 suggested that oxidative coupling of 2-aminobenzophenones might give the 9-acridone system in an analogous manner to that reported for the conversion of 2-hydroxybenzophenones into ~a n t h o n e s . ~ The poor yields which were obtained for this type of cyclisation 5 led us to investigate alternative methods for the ring closure of 2-aminobenzophenones. In our earlier oxidative experiments 2'-amino-2,3,4-trimethoxybenzophenone (1) cyclised to 3,4-dimethoxy-9-acridone (2) in 7% yield, whereas reduction of 2,4,6-trihydroxy-2'nitrobenzophenone (3) gave 1,3-dihydroxy-9-acridone (6; R = H , R 1 = R 2 = OH), quantitatively, presumably via the amine Our interpretation of these cyclisations involved intramolecular displacement of the adjacent ortho-methoxy-group by nucleophilic nitrogen, or, in the case of the amine (4), a Schiff-base-type condensation with the keto-form of the phloroglucinol ring (5). To establish the utility of this type of cyclisation a
The crystal structure of compound [Co2(C14H12N2O2)2] showed dimeric complex. Two nitrogen atoms and two oxygen atoms of the [N,Nbis(salicylidine)diamine] formed distorted square pyramidal geometry in the region of Co(II) and one oxygen atom from each ligand acting as bridge between two ligand molecules which are distorted in parallel path among each other. The titled complex showed amorphous crystalline structure in toluene solvent but to get more clear X-ray crystallographic data three component solvent system (ethanol, toluene, ethyl acetate) was used. The ligand was synthesized and characterized by FTIR, Mass spectrometry, NMR while the titled complex was characterized by FTIR and X-ray crystallography. The ligand and complex were screened for their antibacterial activity against bacterial species Escheria coli, Staphylococcus aureus and Bacillus subtilis and antifungal activity against A. flavus, A. alternate and A. niger. The activity data shows that the metal complex has more antibacterial and antifungal activities than the synthesized ligand against bacterial strains.
Cyclisierung der Acetamido‐(I) (Darstellung beschrieben) oder der Amino‐benzophenone (III) in Gegenwart von NaH liefert die 9‐Acridone (II); (IIa) kann in besserer Ausbeute durch analoge Reaktion des Tosylats (IV) ‐ die Tosyloxygruppe ist eine bessere Abgangsgruppe ‐ gewonnen werden.
Cyclisie‐ rungen der 6‐(o‐Aminobenzoyl)‐5,7‐dimethoxy‐benzochromene (I) liefern Gemische von Acronycin (IIb) bzw. Des‐N‐Methylacronycin (IIa,c) mit entsprechenden Isoacronycinen (III).
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