Refernces
10.1016/j.tet.2020.131861
The study focuses on a Cu(I)-N-heterocyclic carbene (NHC) catalyzed, base-free C-N bond formation reaction involving arylboronic acids and amines or azoles. The primary chemicals used in this study are arylboronic acids, amines, azoles, and Cu(I)-NHC complexes, which serve as the catalysts for the reaction. The purpose of these chemicals is to facilitate the formation of C-N bonds under base-free conditions, which is a significant advancement in the field of organic chemistry, as it potentially offers a more efficient and environmentally friendly method for synthesizing compounds with C-N bonds, which are prevalent in pharmaceuticals and other chemical industries.
10.1039/c6ra01992g
The research focuses on the development of an efficient and regioselective cobalt-catalyzed synthesis method for the creation of multi-substituted pyrroles, which are important five-membered heterocycles found in biologically active natural products and therapeutic agents. The study aims to address the demand for alternative, cost-effective, and environmentally friendly catalysts in organic synthesis. The process relies on the use of readily available enamides and alkynes, with a catalytic amount of Cp*Co(CO)I2 and CuO as the oxidant. The researchers found that this cobalt catalytic system not only constructed carbon-carbon and carbon-nitrogen bonds simultaneously but also exhibited excellent regioselectivity, outperforming palladium catalytic systems. The method tolerated a range of synthetically useful alkynes, leading to the formation of diverse pyrroles in moderate to high yields. The study concludes with the successful development of a cobalt-catalyzed approach for pyrrole synthesis and notes that further investigations into cobalt-catalyzed C-H functionalization for heterocycle construction are ongoing.
10.1080/07391102.2021.1914174
This research focused on the synthesis, characterization, and comprehensive study of nine novel pyrrole-3-one derivatives, with the aim of exploring their dielectric properties, theoretical spectroscopic analysis, molecular docking, and ADME/T properties. The study successfully synthesized the derivatives using furan-3-one derivatives and various aromatic amines, and characterized them using FT-IR, 1H NMR, 13C NMR, and HRMS techniques. The experimental dielectric properties revealed unique behaviors for certain compounds, particularly Ata1, which exhibited negative dielectric values at high frequencies. Theoretical calculations using DFT-B3LYP/6-311++G(d,p) model/level supported the experimental spectroscopic results and provided insights into the electronic transitions and molecular orbitals. Molecular docking studies indicated the compounds' potential as inhibitors for antieczematic/3RZE and CYP2H substrate/3TDA (A chain). The research concluded that the synthesized pyrrole-3-one derivatives possess good pharmacokinetic profiles, making them promising candidates for further drug development studies.
10.1021/op100251q
The study presents the development of a second-generation synthetic process for eletriptan, a drug used to treat migraines, employing a Fischer indole cyclization approach. The new process aims to overcome the limitations of the existing manufacturing route, which includes the use of expensive and harmful starting materials, and generates significant waste. The research details the synthesis of key intermediates, such as aldehyde 8 and hydrazine 10, and explores various methods to improve yield and scalability. The study also discusses the successful application of the Fischer indole reaction to synthesize eletriptan and the optimization of the process using L-ascorbic acid for the reduction of diazonium salts to aryl hydrazines, resulting in a more cost-effective, efficient, and environmentally friendly synthesis route. The final objective was achieved by synthesizing the single enantiomer of eletriptan (R)-7 through classical resolution techniques, offering a potentially more sustainable and scalable method for its production.
10.1016/j.tet.2008.11.036
The research primarily focuses on the arylation reactions of NH-heterocycles, such as pyrazole, 3-(trifluoromethyl)pyrazole, imidazole, and pyrrole, with 2,4-difluoroiodobenzene, facilitated by both copper catalysis and SNAr reactions. The study aims to explore the regioselective reactions and multiple substitutions to synthesize a range of new N-arylated heterocycle derivatives. The reactants include various NH-heterocycles and 2,4-difluoroiodobenzene, with copper catalysts like Cu2O and ligands such as salicylaldoxime utilized in some reactions. The analyses involved the use of 1H, 13C, and 19F NMR spectroscopy, IR spectroscopy, and mass spectrometry to determine the structures and purities of the synthesized compounds, along with X-ray crystallography for certain products to confirm their regiochemistry. The research also includes a Suzuki–Miyaura reaction to extend the utility of the synthesized arylation products.
10.1002/anie.201306511
The research focuses on the development of a traceless directing group strategy for C-H borylation reactions of nitrogen heterocycles and anilines. The main content revolves around the use of the (pinacolato)boron (Bpin) group as a traceless directing group, which can be readily installed and removed without additional steps, offering an alternative to traditional methods that require installation and removal of directing groups. The experiments involved the borylation of various substrates, including pyrroles, indoles, azaindoles, pyrazoles, and anilines, using the Bpin group. Reactants such as HBpin and iridium catalysts were used, along with tertiary amines to facilitate N-borylation. The analyses included monitoring the reactions by 1H and 11B NMR spectroscopy, and evaluating the yields and selectivity of the borylated products. The study demonstrated that the Bpin-directed approach is operationally simpler and generally higher yielding than the Boc-directed counterparts, and it expands the scope of C-H borylation by enabling functionalization at different positions on the substrates.
10.1039/b714412a
The research focuses on the development of a novel porphyrin analogue, m-Benziporphodimethene, as a specific chemosensor for zinc(II) ions (Zn2+). The sensor is designed to exhibit fluorescence "switch-on" upon binding with Zn2+, with no apparent background fluorescence. The study involves the synthesis of the porphyrin analogue through an acid-catalyzed condensation reaction of α,α-dihydroxy-1,3-diisopropylbenzene, pyrrole, and benzaldehyde. The compound was purified using silica gel column chromatography and characterized by its UV-Vis spectrum, which showed broad absorption bands. The non-fluorescent free-base form of the compound changes to a red-emitting solution upon the addition of Zn2+, with a fluorescence quantum yield of 0.34 at the S1 state in degassed toluene at room temperature. The formation of the Zn2+ complex was confirmed through NMR, mass spectrometry, and X-ray single-crystal structure analysis. The chemosensory response was evaluated through spectrophotometric titration and Job plot analysis, demonstrating a 1:1 complex formation with Zn2+ and a high stability constant of 2.05 × 10^5, indicating the sensor's potential for detecting Zn2+ at low concentrations. Selectivity experiments showed that only Zn2+, Hg2+, and Cd2+ turned on fluorescence, with Zn2+ showing the highest fluorescence enhancement. The study also assessed the interference of other metal ions and found that Cu2+, Cr3+, and Ni2+ could quench fluorescence due to their paramagnetic effect, but they did not mimic the presence of Zn2+.
10.1002/adsc.200800490
The study presents an efficient one-pot synthesis method for multisubstituted pyrroles, which are important heterocyclic compounds with applications in pharmaceuticals and materials science. The process involves the reaction of (Z)-enynols with amines or sulfonamides, catalyzed by gold/silver (Au/Ag) or boron trifluoride·etherate/gold/silver (BF3·Et2O/Au/Ag) catalysts, facilitating both amination and cycloisomerization reactions sequentially in a single vessel. Key chemicals used include (Z)-2-en-4-yn-1-ols as precursors, amines or sulfonamides as nucleophiles for amination, and Au/Ag catalysts for promoting the reactions. The purpose of these chemicals is to enable the synthesis of pyrroles with high diversity and regioselectivity under mild reaction conditions, offering a more efficient approach compared to traditional methods.
10.1021/ol900609f
The research discusses a gold-catalyzed synthesis of pyrroles from aryl-substituted N-tosyl alkynyl aziridines, focusing on the significant impact of counterions on the reaction pathway. The study aims to develop a method for synthesizing pyrroles, which are important in biologically active compounds and synthetic intermediates, through a gold-catalyzed ring expansion. The researchers found that the counterion to the gold catalyst determines whether the reaction leads to 2,5-substituted or 2,4-substituted pyrroles. Using cationic gold systems prepared from gold complexes and silver salts with different counterions, they observed that a change in the counterion could alter the reaction's course.
10.1002/ardp.19773100312
The study explores the synthesis of sulfonyl derivatives of Mannich bases derived from quinaldine, pyrrole, and phenol, which are investigated as chemical carriers for germicidal substances. The researchers utilized various sulfones, such as p-toluenesulfone, as starting materials and reacted them with Mannich bases through processes like condensation and addition reactions. Key compounds synthesized include 2-(2'-chinolyl)-1-dimethylamino-3-p-toluenesulfonyl-propan-hydrochlorid (7), 2-benzolsulfonylmethyl-5-dimethylaminomethyl-1-methyl-pyrrol-hydrochlorid (12a), and 3,5-dimethyl-2-morpholinomethyl-6-p-toluenesulfonylmethyl-phenol (15c). These compounds were characterized using techniques such as melting point determination, elemental analysis, and IR spectroscopy. The study aims to develop new chemical forms that can effectively transport germicidal agents, potentially enhancing their stability and application in pharmaceuticals.
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