β Scribed by William Monte; John Stamm
No coin nor oath required. For personal study only.
Abstractz The stmightforward synthesis of 9-[(4_dimeUlylam~)~nyl]-i~~~y~~nium phosphate is described These compounds have bee-n identified as a potent class of aquatic fungicides Acridine derivatives m known to have useful photographic pigment and dye1 pmpertiea. In addition, certain members of this family posse38 antifungal activity.2 Of particular interest is 9-[(4-dimethy~ino)phenyl]-l0-phenylacridiniwn salt 1.
This compound has been identified as having potent antifungal and antiparasitic activity in fish.
The potency of its biological activity is simihu to malachite green 2 a widely used fish fungicide. Phenylacridium salts and malachite m have some topological features in cummon which may account for the similarity ia biilogical activity.
Malachite green is a highly effective fish fungicide. however it has been identified to be a potential carcinogen.
Phmyiacridinium salts were evaluated as alternative marine fungicides.
Phenylacridine salts have been synthesized for use as elcctrophotographic agents.3 They were previously prepared in a multistep synthesis starting with the condensation of N,Ndiphenylanthmnilic acid with phosphorous oxychloride to form N-phenylacridone. Treatment of this ketone with 4dimethylaminophenyl lithium gave the 9-(4-dimethylaminophenyl)-lOphenyl-9-acridanol. This acridanol when exposed to acid leads to the desired acridinium salt 1. A more expeditious route was sought as this synthesis gave low yields.
Compounds of the a&line family can be prepared by a Bemthsen reaction. which involves the coupling of a carboxylic acid and a diphenylamine with zinc chlorkk4 The conditions tend to be quite vigorous and low yielding. It was envisioned that the desired phenylacridine salts1 might be directly prepared, in one step, by a milder Bemthsea procedure.
In this regard Popp reported the successful substitution of Lewis acids with polyphosphoric acid in a modified Bemthsen reaction.5 These milder conditions allow effiiacious formation of acrid&s. He also observed that, ia pmparing &dines under polyphosphoric acid conditions, 9-substituted acridine phosphates were reaction intermediites. While krtiary amines
π SIMILAR VOLUMES
lO-Methyl-acridiniurn-9-(N-suIphonylcarboxamide) salts are prepared via acylation of sulphonamides with acridine-9-carboxylic acid chloride and subsequent N-alkylation with methyl triflate. Substituents on the sulphonamide component were varied to show the effect of steric and electronic factors on