- Magnetic solid sulfonic acid-enabled direct catalytic production of biomass-derived N-substituted pyrroles
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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.
- Li, Hu,Liu, Yixuan,Wang, Keping,Wu, Mei,Yang, Ying
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p. 5312 - 5320
(2022/04/07)
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- Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles
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A new superbase-promoted reaction of acetylene involves self-organization of its three molecules with one molecule of arylamine in KOH/DMSO system to afford 1-aryl-2,5- dimethylpyrroles in up to 63% yields. The key step of this reaction cascade is assumed to be the nucleophilic addition of acetylene to the C = N bond of the intermediate aldimine (aza-Favorsky reaction).
- Schmidt, Elena Yu.,Semenova, Nadezhda V.,Ivanova, Elena V.,Bidusenko, Ivan A.,Trofimov, Boris A.
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p. 109 - 111
(2020/02/29)
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- Indium-mediated one-pot pyrrole synthesis from nitrobenzenes and 1,4-diketones
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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%)
- Lee, Hyunseung,Kim, Byeong Hyo
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p. 6698 - 6708
(2013/07/26)
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- Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3- alkyl-2-(alkylimino)thiazolidin-4-one chemotype
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High affinity and selective S1P4 receptor (S1P4-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H- pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P4-R agonist hit distinct from literature S1P4-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P4-R agonist activity and exquisite selectivity over the other S1P 1-3,5-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P4-R signaling cascade and elucidate the molecular basis of the receptor function.
- Urbano, Mariangela,Guerrero, Miguel,Velaparthi, Subash,Crisp, Melissa,Chase, Peter,Hodder, Peter,Schaeffer, Marie-Therese,Brown, Steven,Rosen, Hugh,Roberts, Edward
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scheme or table
p. 6739 - 6745
(2011/12/05)
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