10.1021/acs.joc.9b00270
The study presents a novel Lewis acid-catalyzed approach for the synthesis of benzofurans and 4,5,6,7-tetrahydrobenzofurans from acrolein dimer and 1,3-dicarbonyl compounds. The method employs N-bromosuccinimide (NBS) as an oxidizing agent and utilizes a combination of Lewis acid catalysts to achieve high yields of 2,3-disubstituted benzofurans. The researchers successfully synthesized two commercial drug molecules, benzbromarone and amiodarone, using this method. The study also explores the substrate scope and optimizes the reaction conditions. Additionally, the authors propose a mechanism involving NBS-assisted auto-tandem catalysis and provide evidence by isolating an intermediate that can be further converted to tetrahydrobenzofurans. This work offers an efficient and practical route to synthesize benzofuran derivatives with potential applications in pharmaceutical chemistry.
10.1080/00397910902898643
The study investigates a three-component reaction involving 5,5-dimethylcyclohexan-1,3-dione (dimedone), aromatic aldehydes, and acetonitrile in the presence of chlorosulfonic acid, resulting in the formation of N-[(2-hydroxy-4,4-dimethyl-6-oxocyclohexene-1-yl)-aryl-methyl]-acetamides. Dimedone acts as a dienophile, aromatic aldehydes serve as the Michael acceptors, and acetonitrile functions as the nucleophile in this reaction. Chlorosulfonic acid is used as a catalyst to promote the reaction. This method provides a straightforward and efficient route for synthesizing these acetamides in good yields, highlighting the utility of multicomponent reactions in generating structurally diverse compounds with potential biological and pharmaceutical relevance.
10.1002/aoc.3815
This study focuses on the synthesis, characterization, and application of nano-CoAl2O4 as an efficient catalyst in the preparation of hexahydroquinolines. The researchers prepared nano-CoAl2O4 using a solution of metal sulfates, polyethylene glycol, and sodium hydroxide, and then calcined it at 800°C for 6 hours. The catalyst was characterized by various techniques including FT-IR, EDX, XRD, SEM, VSM, and TEM. In the synthesis of hexahydroquinolines, nano-CoAl2O4 was used to catalyze the condensation reaction between ethyl acetoacetate, dimedone, and various aldehydes under solvent-free conditions at 80°C. The study demonstrated that the use of nano-CoAl2O4 as a catalyst resulted in high yields, short reaction times, and the ability to reuse the catalyst multiple times without significant loss of efficiency.
10.1016/j.tetlet.2003.11.133
The study presents a concise synthesis method for a novel class of homochiral aromatic amino acid surrogates, featuring tetrahydroindazole or benzisoxazole systems. These surrogates were synthesized through the acylation of cyclic 1,3-diketone by the side-chain carboxyl functionality of specific amino acid precursors, followed by a regioselective condensation with hydrazine, N-benzylhydrazine, and hydroxylamine. The synthetic strategy is versatile, allowing for the creation of structurally diverse derivatives. These novel amino acids can be efficiently incorporated into proteins and have potential applications in imparting unique properties to biological peptides. The study also includes the synthesis of Na-Fmoc-protected derivatives, which are useful for solid-phase peptide assembly, and the exploration of the stereochemistry integrity of the homochiral starting material through chemical transformations. The synthesized amino acids offer opportunities as structural surrogates of tryptophan and as building blocks for designing molecular probes.
10.1007/s11164-018-3659-7
This study presents the synthesis of montmorillonite (MMT) supported Fe3O4 magnetic nanoparticles, which were used as heterogeneous nanocatalysts for the one-pot synthesis of indeno[1,2-b]indolone derivatives in aqueous media. The MMT@Fe3O4 nanocomposites were characterized using various techniques including X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), vibrating sample magnetometer (VSM), thermogravimetric analysis (TGA), and Fourier transform infrared spectroscopy (FT-IR). The catalyst exhibited high efficiency in promoting the cyclocondensation of ninhydrin, 1,3-diketone compounds, and amine derivatives to generate the desired indeno[1,2-b]indolone derivatives in excellent yields under mild conditions. This study highlights the advantages of using MMT@Fe3O4 as an environmentally friendly, cost-effective, and recyclable catalyst, providing a green and efficient approach for the synthesis of these heterocyclic compounds of biological and pharmacological importance.
10.1016/S1872-2067(12)60693-7
The study focuses on the synthesis of 4H-pyran derivatives using a silica-bonded N-propylpiperazine sodium n-propionate (SBPPSP) as a recyclable catalyst. The catalyst was prepared from commercially available and inexpensive starting materials and was used to catalyze the synthesis of various 4H-pyran derivatives, including 3,4-dihydropyrano[c]chromenes, 2-amino-4H-pyrans, 1,4-dihydropyrano[2,3-c]pyrazoles, and 2-amino-4H-benzo[e]chromenes. The chemicals used in the study included aromatic aldehydes, malononitrile, dimedone, ethyl acetoacetate, 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, and α-naphthol, which served as reactants in the multi-component reactions to form the desired 4H-pyran derivatives. The purpose of these chemicals was to participate in condensation reactions under refluxing aqueous ethanol conditions, with SBPPSP facilitating the process and being easily recoverable and reusable, highlighting the environmental and economic benefits of the method.
10.1002/jhet.322
The study presents a green chemical procedure for the synthesis of 1,8-dioxodecahydroacridine derivatives under microwave irradiation in aqueous media without the use of a catalyst. The method offers advantages such as high yields (86-96%), a simple workup procedure, and environmental friendliness. The chemicals used in the study include various aromatic aldehydes, dimedone or 1,3-cyclohexanedione, and primary arylamines, which react under the specified conditions to form the target 1,8-dioxo-decahydroacridine derivatives. These compounds are significant due to their potential applications in pharmaceuticals, particularly as treatments for cardiovascular disorders and as calcium channel blockers, and also as photoinitiators. The study demonstrates that the electronic properties of the substituents on the aromatic rings do not significantly affect the reaction, and the method is applicable to a wide range of arylamines, including those with electron-withdrawing and electron-donating groups.
10.1021/jo01353a009
The study explores the synthesis of various substituted naphthyridines and biphenyls through different chemical reactions. Key chemicals involved include N-(3-amino-4-picolylidene)-p-toluidine, which serves as a precursor for multiple reactions to produce compounds like 1,7-naphthyridine-2-aldoxime, 2,9-diaza-6,8-dihydro-7,7-dimethyl-5-oxoanthracene, and 7,9-diazabenz[f]indane. These compounds are formed by reacting the precursor with different reagents such as isonitrosoacetone, dimethyldihydroresorcinol, and cyclopentanone under specific conditions like heating and refluxing. The products are characterized by their melting points, yields, and elemental analysis. In another part of the study, the reaction of various p-aroylpropionic acids with benzoyl chloride is investigated, yielding substituted phthalides in the biphenyl series. The study also delves into the infrared and ultraviolet spectral analysis of these products to understand their structural properties.