A new intramolecular cyclisation reaction—I : Novel synthesis of benzo(k,1)thioxanthene-3,4-dicarboxylic anhydride and derived dyestuffs |
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| Authors: | AM Kadhim AT Peters |
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| Institution: | Dyestuffs Research Laboratories, School of Colour Chemistry and Colour Technology, The University, Bradford BD7 1DP, England UK |
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| Abstract: | A new direct synthesis of benzo(k,1)thioxanthene-3,4-dicarboxylic anhydride from 4-nitro-naphthalene-1,8-dicarboxylic anhydride and 2-aminobenzenethiol is reported; 4-(2-aminophenylthio) naphthalene-1,8-dicarboxylic anhydride and 4-phenylthionaphthalene-1,8-dicarboxylic anhydride are also formed. Similar reaction in presence of amyl nitrite or sodium nitrite results in formation of larger amounts of 4-phenylthionaphthalene-1,8-dicarboxylic anhydride, together with other products arising from the oxidation of 2-aminobenzenethiol; one such product is the new heterocycle 9,10-dithiaphenanthrene. 4-(2-Aminophenylthio)-naphthalene-1,8-dicarboxylic anhydride is rapidly converted by amyl nitrite or sodium nitrite in dimethylformamide into benzo(k,1)thioxanthene-3,4-dicarboxylic anhydride, constituting a novel one-stage intramolecular cyclisation reaction of greater convenience than the conventional two stage Pschorr cyclisation. |
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