Synthetic Utilization of PolynitroaromaticCompounds: Synthesis of Fluorinated FusedHeterocycles from Polynitroaromatic Compounds

摘要

Methods for the preparation of fluorinated benzo[d]-isothiazoles, benzo[d]isothiazol-3(211)-ones and benzo[b]-thiophenes from available 2,4-di- and 2,4,6-trinitrotoluenes aredescribed. One of them entails fluoro- or trifluoroethoxy-denitration of corresponding nitro- or dinitroheterocyclesobtained from polynitrotoluenes. An alternative approach isbased on a stepwise regioselective substitution of nitro groupsin polynitrotoluenes or polynitrobenzoic acid derivatives(amides, nitriles) with S-, 0- and F-nucleophiles followed byheterocyclic ring closure. The methods were applied for the conversion of polynitroaromatic compounds to pharma-cologically–useful fused heterocycles.