Article
Chemistry, Multidisciplinary
Raziyeh Keshavarz, Mahnaz Farahi, Bahador Karami, Parisa Gheibipour, Ali Zarnegaryan
Summary: A heterogeneous catalyst with a high contact surface, excellent performance, and recyclability was successfully prepared using graphene oxide as a support. The catalyst showed satisfactory performance in the synthesis of pyrroles and could be easily recovered and reused.
ARABIAN JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Physical
Sambasivarao Kotha, Deepshikha Singh
Summary: In this paper, three simple methods for the synthesis of pyrrole derivatives starting with commercially available amines were reported. The first method achieved one-pot ring closing metathesis (RCM) and aromatization sequence using Grubbs first-generation catalyst (G-I), without the use of any additional reagents. The second and third methods relied on the condensation of 2,5-hexanedione/2,5-dimethoxy tetrahydrofuran in the presence of a low melting mixture of N, N'-dimethylurea (DMU) and L-(+)-tartaric acid (TA) and glacial acetic acid, resulting in substituted pyrroles with excellent yield. The photophysical properties of these molecules were also studied by fluorescence spectroscopic data, showing good quantum yield (OF).
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Sachin B. Wagh, Vladimir Maslivetc, James J. La Clair, Alexander Kornienko
Summary: Recent studies have discovered the ability of human prostaglandin-endoperoxide synthase 2 (COX-2) to guide the formation of fluorescent pyrroles through a specific reaction, leading to the identification of a central motif. Further exploration of this motif has resulted in the design of COX2 inhibitors with comparable activity to the orally prescribed nonsteroidal anti-inflammatory COX-2 inhibitor Celecoxib. Additionally, important structure-activity relationship (SAR) data for the discovery of COX-2 inhibitors has been obtained.
Article
Chemistry, Multidisciplinary
Gabriella Leonardi, Ada Truscello, Grazia Isa C. Righetti, Giovanni Gennaro Mondrone, Luca Mascheroni, Attilio Citterio, Roberto Sebastiano
Summary: Pyrroles are important compounds utilized in drug synthesis and material chemistry. This study presents a sustainable synthesis of N-substituted pyrrole carboxylic acid derivatives using 3-hydroxy-2-pyrones as the masked 1,4-dicarbonyl compounds that efficiently react with primary amines. The reactions can be carried out under sustainable conditions, obtaining pyrroles with high yields.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Organic
Robert H. E. Schirmacher, Daniel Roesch, Franziska Thomas
Summary: An additive-free synthesis of challenging N-substituted aryl pyrroles from poorly soluble 1,4-diketones using HFIP as a solvent and reaction promotor is reported. The procedure offers simple execution and purification, and can be applied to a variety of structurally diverse pyrroles. HFIP can also be used as a solvent in the Paal-Knorr synthesis of furans and thiophenes, with a more pronounced solvent effect observed in pyrrole synthesis.
Article
Chemistry, Physical
Mojgan Zendehdel, Soheila Khaghaninejad, Arezoo Kheiri
Summary: In this study, an acid catalyst was synthesized by functionalizing 1-Butyl-3-methyl imidazolium azide on zeolite, resulting in a catalyst with micro-meso structure, high surface area, and good acidity. The catalyst was used for the synthesis of pyrrole derivatives under solvent-free conditions, showing high yield.
Article
Chemistry, Physical
Yamei Lin, Fei Wang, Enxiang Ren, Fuying Zhu, Qiang Zhang, Guo-Ping Lu
Summary: The development of novel iron heterogeneous catalysts for organic synthesis is attractive and significant for both academic and industrial applications. A carbon-based iron heterogeneous catalyst (Fe@NSiC) comprising of different iron species including iron atomic single sites (FeNxSiy), iron silicate, and iron nanoparticles (NPs) has been developed. This catalyst exhibits high performance on the solvent-free synthesis of pyrroles from nitroarenes and 2,5-hexanedione via cascade reaction using HCOOH/DBU as the reductant, and a set of pyrroles reflecting potential interest from the pharmaceutical perspective are obtained with moderate to excellent yields in this chemistry.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Kioumars Aghapoor, Farshid Mohsenzadeh, Hossein Reza Darabi, Hani Sayahi
Summary: This study demonstrated the exceptional catalytic activity of crystalline salicylic acid as an organocatalyst in solvent-free Paal-Knorr pyrrole synthesis under microwave activation. It showed high efficiency even under low microwave power irradiation or shorter reaction times, and enabled ultrafast pyrrole synthesis with no risk of metal contamination.
JOURNAL OF CHEMICAL SCIENCES
(2021)
Article
Chemistry, Physical
Yusuf Ajibola Ibrahim, Jiahui Li, Liankun Ai, Baolin Li
Summary: A total of 23 new pyrrole compounds were successfully synthesized in this study, including tetra- and penta-substituted pyrroles which are known to be synthetically challenging. The method utilized a cheap catalyst, simple experimental setup, scalability, and achieved excellent yields. Some selected pyrroles exhibited strong blue fluorescence with considerable Stokes shifts.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Biochemistry & Molecular Biology
Roman O. Shcherbakov, Diana A. Eshmemet'eva, Anton A. Merkushev, Igor V. Trushkov, Maxim G. Uchuskin
Summary: A new approach to 3-(furan-2-yl)-1,3-di(het)arylprop-2-en-1-ones has been developed through the oxidative dearomatization and cyclization of di(het)aryl-substituted 2-ene-1,4,7-triones, showing high synthetic efficiency.
Article
Chemistry, Organic
Naresh Vempala, Anireddy Jaya Shree, Srikanth Reddy Narra, Somnath Dasgupta
Summary: A concise and efficient synthesis method for the production of atorvastatin calcium, a key cholesterol-lowering drug, has been presented.
Article
Chemistry, Physical
Omar Portilla-Zuniga, Oscar M. Bautista-Aguilera, Jose J. Martinez, Hugo Rojas, Mario A. Macias, Isabel Iriepa, Adrian Perez-Redondo, Angel Sathicq, Juan-Carlos Castillo, Gustavo P. Romanelli
Summary: The Paal-Knorr reaction of acetonylacetone with primary amines catalyzed by CATAPAL 200 under conventional heating at 60 degrees C for 45 min resulted in N-substituted pyrroles in yields of 68-97%. CATAPAL 200, with its high percentage of Bronsted-Lewis acid sites (23%) and pore diameter (37.8 nm), promotes the formation of pyrrole ring by facilitating condensation and dehydration processes. This protocol offers simplicity, high yields, reduced reaction time, solvent-free conditions, stoichiometric amounts of reactants, low catalyst loading, and clean reaction profile. Furthermore, CATAPAL 200 is inexpensive and readily available, making it a cost-effective option for chemical transformations. The catalyst can be reused for up to five cycles without significant loss of catalytic activity, making this protocol sustainable and advantageous compared to conventional methods.
Article
Chemistry, Multidisciplinary
Asieh Azhdari, Najmedin Azizi, Haleh Sanaeishoar, Elham Tahanpesar
Summary: A novel heterogeneous acidic catalyst was prepared by immobilizing amidosulfonic acid on graphitic carbon nitride, leading to a unique solid acid structure that enhanced catalytic activity for the high efficient preparation of pyrroles. The catalyst showed good to excellent yields with simple purification and maintained its activity after multiple cycles.
MONATSHEFTE FUR CHEMIE
(2021)
Article
Chemistry, Multidisciplinary
Deng-Yue Zheng, Tianjian Zhang, Rongxian Bai, Minghao Li, Ruifeng Wang, Yanlong Gu
Summary: Based on the confinement effect of MOFs, a straightforward method for synthesizing unsymmetrically substituted NH-pyrroles from alpha-hydroxyketone and 3-aminocrotonate was developed. The confined space of the pore channels limited the potential overreaction, allowing for good control of the reaction selectivity. This synthesis route also offers a new strategy for utilizing bio-based platform molecules.
Article
Chemistry, Multidisciplinary
Ibrahim Yusuf Ajibola, Liankun Ai, Baolin Li
Summary: Phosphoric acid catalyzes the cyclization reaction of 1,4-dicarbonyl compounds to produce a variety of arylfuran compounds efficiently. The method is advantageous due to its organic-solvent-free system, wide substrate scope, and excellent yields.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)