Collect. Czech. Chem. Commun. 1988, 53, 1761-1769

3-pyridiniumindolyl-2-thiolates - New type of functionalized indoles

Jozef Gonda and Pavol Kristian

Department of Organic Chemistry, P. J. Šafárik University, 041 67 Košice


2-Bromomethylphenyl isothiocyanate (I) reacts with pyridines to give 2-isothiocyanatobenzylpyridinium bromides II. Deprotonation of these compounds with sodium ethoxide in ethanol of sodium hydride in dimethyl sulfoxide afforded novel type of functionalized indoles, 3-pyridiniumindolyl-2-thiolates. Reaction of II with KOH or KCN gave products of addition to the NCS group VII and VIII, respectively. Structure of the obtained compounds was proven by IR, 1H NMR, 13C NMR, and mass spectra and was confirmed by X-ray diffraction analysis of 3-pyridiniumindolyl-2-thiolate.