Aromatic nucleophilic substitution. Part 2. Preparation of novel 3-substituted xanthone and thioxanthone derivatives

The novel 3-nitro-9-oxo-9H-xanthene- and 3-nitro-9-oxo-9H-thioxanthene-l-carboxylic acids 2a–d were prepared by intramolecular acylation of 3-aryloxy- and 3-arylthio-5-nitrophthalic anhydrides 1 (Scheme). The 3-nitro group was readily substituted by O- and S-nucleophiles and halide and azide ions to give a range of 3-substituted thioxanthone derivatives 3 with varied λ_max.