Synthesis of 4-aryloxy-7-nitrobenzofurazan Derivatives from 4-chloro-7-nitrobenzofurazan and Various Phenoxide Anions (Including Pharmaceuticals) in the Presence of Crown Ethers

摘要

4-Chloro-7-nitrobenzofurazan reacts by nucleophilic substitution with phenoxide anions derived from estriol (2c), ethynylestradiol (2d), phenol (3e), guaiacol (3f), 2,6-dimethoxyphenol (3g), eugenol (3h), isoeugenol (3i), the cytostatic Etoposide (4), and Reichardt's betaine (5) in the presence of crown ethers affording the corresponding 4-aryloxy-7-nitrobenzofurazan derivatives 6c, 6d, 7e - 7i, 8, and 9. The structure of these compounds was confirmed by NMR spectra. Hydrophobicity/hydrophilicity parameters were investigated by reverse phase thin-layer chromatography.