Synthetic Exploitation of Halogenated Alkenes Containing EWG: Polysubstituted Sulfanyl Dinitro Butadienes from Sequential Nucleophilic Substitutions

Abstract

Our novel approach starts from a 1,1,3,4-tetrachloro-2,4-dinitrobuta-1,3-diene (5) being one of the most prominent members of this relatively new class of synthetic building blocks. Because of its multifunctional chemical behavior, polyhalogenated nitrobuta-1,3-dienes proved to be versatile reagents in the synthesis of a large variety of sulfurated, (hetero) cyclic, and acyclic derivatives. We describe our studies concerning successive nucleophilic vinylic substitution reactions of dinitrobuta-1,3-diene in order to establish the reactivity profile of this precursor and determine whether this precursor could be used for the synthesis of many dinitrodiene analogues offering new methodology for the synthesis of polyfunctional precursors that are difficult to access. Some of the resulting perfunctionalized 2,4-dinitrobuta-1,3-dienes are subjected to further transformations to give promising candidates with respect to biological activity.