Synthesis of substituted diphenylamines and carbazoles: phototransformation products of diclofenac |
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Authors: | Jesper Svanfelt Leif Kronberg |
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Institution: | 1. Laboratory of Organic Chemistry, ?bo Akademi University, Biskopsgatan 8, 20500, Turku, Finland
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Abstract: | The formation of stable and potentially hazardous compounds as a result of photochemical transformation of pharmaceutical
substances in the aquatic environment implies a demand for standard compounds within environmental analysis. The major phototransformation
products of diclofenac are comprised of substituted diphenylamines and carbazoles. Substituted diphenylamines were synthesized
by Ullmann condensation reactions between anilines and halobenzenes. Monochlorocarbazoles were obtained from palladium-catalyzed
intramolecular coupling reactions of monochlorinated diphenylamines, photocyclization of dichlorinated diphenylamines or by
direct chlorination of carbazole. The availability of synthetic photoproducts of diclofenac is of critical importance for
further studies on the environmental fate as well as the ecotoxicological effects of the drug in the environment. |
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