One-pot four-component synthesis of 4-hydrazinothiazoles: novel scaffolds for drug discovery

One pot ring synthesis of novel 4-hydrazinothiazoles through sequential four-component route employing carbonyl compounds, aminoguanidine, isothiocyanates, and alpha-haloketones was accomplished under mild reaction conditions. Base-assisted eliminative aromatization in the [4+1] ring synthesis shed light on interesting leaving group propensities of amine versus hydrazine resulting in the exclusive formation of the title compounds with immense potential as scaffolds for drug discovery. Hydrazone deprotection was effected by acylation which subsequently provided a new set of diacylated molecular systems with a wider scope as chemical handles in the design of thiazolyl drug candidates. (C) 2014 Elsevier Ltd. All rights reserved.