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Oxidation and reduction of sulfamethoxazole

Oxidation and reduction of sulfamethoxazole (SMX, 1) was studied under various reaction conditions. Oxidation reaction by hydrogen peroxide in glacial acetic acid afforded predominately the corresponding nitro derivative 2 (SMX-NO2). When the reaction was catalyzed by methylrhenium trioxide (MTO) the main product was azoxy derivative 3 (SMX-AZ). Catalytic hydrogenation of SMX with Pd/BaSO4 and the substrate/catalyst mass ratio 1:1 resulted with amidine 4 (SMX-AD). The compound 4 was obtained by hydrogenation of nitro compound 2 under the same reaction conditions. Hydrogenation of 2 in the presence of PtO2 and triethyl phospite (TEP) and substrate/catalyst ratio 10:1 gave the hydroxylamine 5 (SMX-HA). Reduction of 2 by zinc dust gave the same product. Selective oxidation of 5 led to nitroso compound 6 (SMX-NO).

sulfamethoxazole; oxidation; reduction

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