146135-21-9Relevant articles and documents
Magnetic solid sulfonic acid-enabled direct catalytic production of biomass-derived N-substituted pyrroles
Li, Hu,Liu, Yixuan,Wang, Keping,Wu, Mei,Yang, Ying
, p. 5312 - 5320 (2022/04/07)
Five-membered nitrogen heterocyclic pyrroles have extremely high physiological activity and are widely used in medicine, agriculture, materials chemistry, industry, and supramolecular chemistry. Developing a mild and eco-friendly way to synthesize functionalized pyrroles from biologically derived materials is desirable. In this study, biomass-derived 2,5-dimethylfuran can react with a series of aromatic amines to synthesize 2,5-dimethyl-N-arylpyrroles through acid-enabled ring-opening and Paal-Knorr condensation in one pot. Among the tested acid catalytic materials, a new magnetic biocarbon-based sulfonic acid solid catalyst (WK-SO3H) showed excellent catalytic performance in the synthesis of N-substituted pyrroles (up to ca. 90% yield) and was easy to separate and recover by an external magnetic field. The ring-opening of furan proved to be the rate-determining step of the above one-pot multi-step conversion process, and 2,5-hexanedione is a key intermediate for the cascade reaction, while the addition of water could significantly enhance the above-mentioned ring-opening reaction. Furthermore, multiple characterization methods (e.g., FT-IR, TGA, XRD, NH3-TPD, and XPS) confirmed that WK-SO3H has good stability in the aqueous reaction system.
Indium-mediated one-pot pyrrole synthesis from nitrobenzenes and 1,4-diketones
Lee, Hyunseung,Kim, Byeong Hyo
, p. 6698 - 6708 (2013/07/26)
One-pot reduction-triggered heterocyclizations of nitrobenzene derivatives with 1,4-diketones were investigated. In the presence of indium/AcOH in toluene at 80 C, reaction of nitrobenzenes with 2,5-hexadione produced moderate to excellent yields (40-98%)