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Relevant academic research and scientific papers

Synthesis of magnetic chitosan supported metformin-Cu(II) complex as a recyclable catalyst for N-arylation of primary sulfonamides

The application of chitosan, which has received much attention as a natural polymer and effective support, has many advantages such as biodegradability and biocompatibility. In this study, the immobilization of a copper complex on the magnetic chitosan bearing metformin ligand has been developed through immobilizing structurally defined metformin with long tail of (3-chloropropyl)trimethoxysilane (TMOS). The synthesized Fe3O4-chitosan@metformin-Cu(II) complex (Fe3O4-CS@Met-Cu(II)) was used as an effective, reusable and magnetic catalyst in the N-arylation of different derivatives of primary sulfonamides with arylboronic acids in ethanol. The primary sulfonamides were prepared from the reaction of sulfonyl chlorides with sodium cyanate in water under ultrasonic irradiation. Utilizing a wide variety of substrates in EtOH as a green solvent, high yields of the primary and secondary sulfonamides, easy work-up along with the excellent recovery and reusability of the catalyst, make this process a simple, economic and environmentally benign method. The synthesized Fe3O4-CS@Met-Cu(II) was characterized using various techniques such as XRD (X-ray diffraction), EDS (energy-dispersive X-ray spectroscopy), elemental mapping, TEM (transmission electron microscopy), FESEM (field emission scanning electron microscopy), VSM (vibrating sample magnetometer), ICP-MS (inductively coupled plasma mass spectroscopy), TGA (thermogravimetric analysis) and FT-IR (Fourier-transform infrared spectroscopy) analyses. The catalyst can be recycled and reused 5 times with no considerable loss of catalytic activity.

Sulfonamide compound and metal-free catalytic construction method and application thereof

The invention discloses a sulfonamide compound as shown in a formula (I) which is described in the specification and a synthesis method thereof. A series of sulfonamide compounds are obtained throughreaction of nitroaromatic hydrocarbon, an inorganic sulfur reagent and boric acid as reaction raw materials in a solvent under the action of alkali and an additive. Metal catalysis and an additional reducing agent are not needed, an inorganic sulfur reagent is used as a sulfur source and a reducing agent, and a series of sulfonamide compounds are constructed in one step by a three-component one-pot method. The invention also discloses an application of the sulfonamide compound in synthesis of sulfonamide drugs. The raw materials of the synthesis method are wide in source, cheap and easy to obtain; the reaction operation is simple; the substrate universality is high; and the synthesis method is economic and practical. The sulfonamide compound has high practical value and a wide applicationprospect.

Straightforward Sulfonamidation via Metabisulfite-Mediated Cross Coupling of Nitroarenes and Boronic Acids under Transition-Metal-Free Conditions?

A straightforward multicomponent sulfonamidation of nitroarenes, sodium metabisulfite and boronic acids was established under transition-metal-free conditions to access diverse sulfonamides from readily available and low-cost materials modularly. Inorganic salt sodium metabisulfite not only served as a sulfur dioxide source, but also played a key role for both activator and reductant during sulfonamidation. Notably, naturally occurring biomolecules and pharmaceuticals with multiple heteroatoms and sensitive functional groups were intensively investigated in this transformtion providing versatile sulfonamides collectively. Further mechanistic studies demonstrated that nitrosoarene is the key intermediate, and the activation of boronic acid is the rate-determining step in the transformation.

Copper-catalyzed redox coupling of nitroarenes with sodium sulfinates

A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.

Fe-based metal-organic frameworks for the synthesis of N-arylsulfonamides via the reactions of sodium arylsulfinates or arylsulfonyl chlorides with nitroarenes in water

A newly developed chemoselective reaction of sodium arylsulfinates or arylsulfonyl chlorides with nitroarenes has been disclosed. The chemistry, in which non-toxic water and recyclable iron-based metal-organic frameworks are employed as the solvent and catalyst, respectively, provides an efficient approach for the generation of N-arylsulfonamides, which are widely present in biologically active compounds and drugs, rendering this methodology attractive to both synthetic and medicinal chemistry.

Copper-catalyzed cross-coupling of chloramine salts and arylboronic acids in water: A green and practical route to N-arylsulfonamides

A green and practical method for the synthesis of N-arylsulfonamides from chloramine salts and arylboronic acids is herein developed. The reaction proceeds readily in the presence of 5 mol% of CuI and 2.5 equiv. K2CO3 in water at room temperature, generating a variety of N-arylsulfonamides in moderate to good yields with good functional group tolerance.

Synthesis of N -Arylsulfonamides by a Copper-Catalyzed Reaction of Chloramine-T and Arylboronic Acids at Room Temperature

A copper-catalyzed Chan-Lam-coupling-like reaction of a (het)arylboronic acid and chloramine-T (or a related compound) has been developed for the synthesis of N -arylsulfonamides at room temperature in moderate to good yields, with good tolerance of functional groups. In this process, it is believed that chloramine-T serves as an electrophile.

Inhibitors of viral entry into mammalian cells

The present invention is related to the development of compounds and methods for inhibiting viral infection in a mammal. A pseudotype virus was developed for use in a high throughput assay for identifying nonpeptidic small molecule inhibitors that prevent

Synthesis and screening of in vitro antibacterial and enzyme inhibitory activity of N,N-disubstituted 4-chlorobenzenesulfonamides

Sulfonamide, pharmacologically important class of compounds, is of significant interest for scientists due to increased resistance in microbes against the existing drug constituents. So the aim of following research work was to synthesize new more effecti

Natural Indian Natrolite zeolite-supported Cu nanoparticles: A new and reusable heterogeneous catalyst for N-arylation of sulfonamides with boronic acids in water under ligand-free conditions

We report here on the preparation of primary sulfonamides and efficient, easily recoverable and reusable copper nanoparticles supported on natural Indian Natrolite zeolite as a catalyst for arylation of sulfonamides with arylboronic acids in water. The catalyst was characterized using the powder XRD, SEM, EDS and FT-IR spectroscopy. The significant advantages of this methodology are high yields, elimination of organic solvents, and simple work-up procedure. The catalyst was easily isolated from the reaction mixture and reused with no significant loss in its activity.