Central European Journal of Chemistry
Volume 1, Number 3, 260-276, DOI: 10.2478/BF02476228

Synthesis of 4-aryloxy-7-nitrobenzofurazan derivatives from 4-chloro-7-nitrobenzofurazan and various phenoxide anions (including pharmaceuticals) in the presence of crown ethers

Marioara Bem, Miron T. Caproiu, Dan Stoicescu, Titus Constantinescu and Alexandru T. Balaban

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Abstract

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.

Keywords   4-aryloxy-7-nitrobenzofurazan derivatives  -  phenoxide anions  -  4-chloro-7-nitrobenzofurazan  -  crown ethers  -  NMR spectra  -  RPTLC

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