Synthesis and Properties of Bisthiadiazoles with Ethyl and Butyl Spacers

Abstract

This article is devoted to a selection of the most effective preparative method for the synthesis of bis(5-amino-1,3,4-thiadiazole-2-yl)alkanes. These compounds are binuclear diamines consisting of symmetrical 1,3,4-thiadiazole fragments connected by alkyl spacers of various lengths. The structures of the obtained compounds were determined by IR spectroscopy, mass-spectrometry and elemental analysis. The possibility of using these molecules as precursors for the synthesis of macroheterocyclic compounds with expended coordination cavity consisting of six small cycles was demonstrated. Optimal synthesis conditions of bis(5-amino-1,3,4-thiadiazole-2-yl)ethane and bis(5-amino-1,3,4-thiadiazole-2-yl)butane were found by variation of reaction time and temperature. Virtual screening of the obtained compounds was carried out in order to predict antibacterial and biological activities as well as toxic properties of the targeted products. On the basis of the known literature data on polynuclear diamines, the exhibition of the liquid crystal properties of the synthesized molecules is supposed.