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New synthetic approach for preparation of fluorinated benzo[d]isothiazoles, benzo[d]isothiazol-3(2H)-ones and benzo[b]thiophenes from available 2,4-di- and 2,4,6-trinitrotoluenes has been developed. The synthesis entails oxidation of the polynitrotoluenes to corresponding polynitrobenzoic acids with aqueous nitric acid at high temperature and pressure, stepwise displacement of the nitro groups in the 2,4-di- and 2,4,6-trinitrobenzamides (-nitriles) with S-, O-, and F- nucleophiles followed by the ring closure. Fluoro- or trifluoroethoxy- denitration of the nitroheterocycles was also employed in some cases. Among prepared compounds are fluorinated analogs of antiviral agents and enzyme inhibitors. The proposed methodology may be considered as an approach to the chemical utilization of polynitroaromatic compounds for the synthesis of valuable chemical products.