560993-95-5

Usage

Uses

Used in Chemical Synthesis:
5-thiophen-3-yl-furan-2-carboxylic acid is used as a reactant in the palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryland heteroaryltrifluoroborates. This application is significant because the Suzuki-Miyaura cross-coupling is a widely employed method for the formation of carbon-carbon bonds, which are essential in the synthesis of various complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
In the context of the Suzuki-Miyaura cross-coupling, 5-thiophen-3-yl-furan-2-carboxylic acid serves as a valuable building block for the construction of diverse molecular architectures. The thiophene and furan rings provide opportunities for further functionalization and modification, making 5-thiophen-3-yl-furan-2-carboxylic acid a versatile starting material for the development of new molecules with potential applications in various industries.

Upstream product

• 585-70-6 5-bromo-furan-2-carboxylic acid 
• 2527-99-3 methyl 5-bromo-2-furoate 
• 1276591-90-2 C₁₀H₈O₃S 

Relevant academic research and scientific papers

Synthesis and Antimicrobial Evaluation of Nitazoxanide-Based Analogues: Identification of Selective and Broad Spectrum Activity

A library composed of nitazoxanide-based analogues was synthesized and assayed for increased antibacterial efficacy against the pyruvate-ferredoxin oxidoreductase (PFOR) using microorganisms Helicobacter pylori, Campylobacter jejuni and Clostridium difficile. Derivatives were found to recapitulate and improve activity against these organisms and select analogues were tested for their ability to disrupt the PFOR enzyme directly. The library was also screened for activity against staphylococci and resulted in the identification of analogues capable of inhibiting both staphylococci and all PFOR organisms at low micromolar minimum inhibitory concentrations with low toxicity to human foreskin cells. Hitting them where it hurts! A library of nitazoxanide-based analogues was synthesized and assayed for antibacterial efficacy against pyruvate-ferredoxin oxidoreductase (PFOR) utilizing microorganisms. Derivatives were found to recapitulate and improve activity against these organisms, and select analogues were screened for activity against staphylococci resulting in the identification of analogues capable of inhibiting both staphylococci and all PFOR organisms at low micromolar minimum inhibitory concentrations.

Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates

An extended study of the reactivity of potassium aryl- and heteroaryltrifluoroborates in Suzuki-Miyaura cross-coupling reactions is presented. The coupling of aryl- and electron-rich heteroaryltrifluoroborates with aryl and activated heteroaryl bromides proceeds readily under ligandless conditions. When deactivated aryl- and heteroaryltrifluoroborates are coupled with aryl and heteroaryl bromides and chlorides, a low loading (0.5-2%) of PdCl2(dppf)·CH2Cl2 efficiently catalyzes the reactions. Under either condition, reactions can generally be carried out in an open atmosphere.