Recent developments in the chemistry of 2-thienylpyrroles: synthesis, reactivity and applications

Abstract

Recent advances concerning the synthesis, reactivity and potential applications of 2-thienylpyrroles are reported in the present review. Thienylpyrroles play important roles in natural product chemistry, agriculture, materials science and medicinal chemistry. In materials science they have found applications as nonlinear optical chromophores, conducting polymers, and anion binding agents, while in medicinal chemistry, they are important building blocks for the synthesis of antitumor agents displaying also antiviral, antibacterial, antifungal, antiinsecticidal and antiherbicidal activities. Therefore the deevelopment of efficient methods for the synthesis of these compounds has become an important and topical area of heterocyclic chemistry. In our laboratories we have developed a convenient method for the syntheis of 1-alkyl(aryl)-2-thienylpyrroles, through the combination of the Friedel-Crafts and Lawesson reactions. 1-Alkyl(aryl)-2-thienylpyrroles, were used as precursors in several type of reactions, allowing the preparation of a variety of new donor-acceptor substituted thienylpyrroles. The characterization of the solvatochromic, optical (linear and nonlinear) and thermal properties of the new pi-conjugated push-pull systems are described. The prospects of application of the new compounds are also discussed. Particular attention has been paid to their application as solvatochromic probes and as efficient and thermally stable nonlinear optical materials.