Synthesis of new 2-(thiazol-2-ylidene) malononitrile, and 2-(1,3-selenazol-2-ylidene) malononitrile derivatives via nitroepoxide ring opening with malononitrile-isothiocyanate (or isoselenocyanate) adducts

Abstract

In line with recent research on the synthesis of five-membered heterocyclic compounds, the synthesis of novel derivatives of 2-(1,3-selenazol-2-ylidene) malononitrile and 2-(thiazol-2-ylidene) malononitrile was carried out via the ring opening of nitroepoxide as an efficient starting material in this study. This reaction was carried out via the formation of malononitrile-isothiocyanate (or isoselenocyanate) adducts, followed by the addition of nitroepoxide to synthesize the products with easy purification. The effectiveness of this process was demonstrated through a gram-scale experiment, performing the four-component reaction, without the addition of a catalyst, at room temperature and in acetone solvent. 18 new heterocyclic compounds from the new 1,3-selenazoles and thiazoles family were synthesized and identified, and confirmed by IR, Mass, and NMR analyses.