9-Isothiocyanatoanthracene as a Versatile Starting Compound in the Chemistry of Anthracen-9-yl Derivatives

Abstract

The synthesis, structure and reactivity of 9-isothiocyanatoanthracene (5) likewise the conformation of the corresponding thioureas (6a-6i) have been studied. The 13C NMR substituent chemical shift values of the NCS group and correlations between spectral parameters (IR, NMR) and rate constans of reactions of 5, acridin-9-yl (14), phenyl (15) and benzoyl isothiocyanate (16) with butylamine were found. Significant increase of the fluorescence of the synthesized anthracenylthioureas with amino acid rests refers to the possibility to use 5 as potential biomarker.