Sulfur-containing organic molecules have frequently been linked to the cancer problem, in respect either to the mechanism (1) or to the inhibition (2) of chemical carcinogenesis. In view of the activity of angular benzocarbazoles and dibenzocarbazoles as tumor-producing agents (3), derivatives of these bearing thioether groups have now been synthesized for biological investigation.2From results published in previous papers of this series (4), 7-methylmercapto-1-tetralone (III) was deemed a particularly convenient intermediate for such syntheses. We prepared this hitherto unknown ketone very easily by the following sequence of reactions: (a) Friedel-Crafts' condensation of succinic anhydride with thioanisole, to give /3-(4-methylmercaptobenzoyl)propionic acid (I); (b) reduction of the foregoing compound to 7-(4-methylmercaptophenyl)butyric acid (II) by the Wolff-Kishner reaction, using the convenient modified technique of Huang-Minlon ( 5); (c) conversion of the acid (II) into its chloride by thionyl chloride and cyclization of the latter with aluminum chloride into 7-methylmercapto-1-tetralone (III).Each of these reactions was achieved with high yields, but it was found in the final stage that the use of benzene as a solvent for cyclization resulted in poor yields of the cyclic ketone (II), owing to the competitive formation of 4-(methyl-SUMMARY 1. The preparation of 7-methylmercapto-1 -tetralone is described.2. The use of the foregoing ketone for the synthesis of sulfur-containing carbazole and acridine derivatives is reported.
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