33757-60-7

Upstream product

• 578-66-5 8-amino quinoline 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 

Downstream Products

• 1438425-63-8 [(N-quinoline-8-yl-4-methoxybenzenesulfonamido)(p-cymene)chlororuthenium(II)] 

Relevant academic research and scientific papers

Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group

The use of cobalt as catalyst in direct C-H activation protocols as a replacement for more expensive second row transition metals is currently attracting significant attention. Herein we disclose a facile cobalt-catalyzed C-H functionalization route towards sultam motifs through annulation of easily prepared aryl sulfonamides and alkynes using 8-aminoquinoline as a directing group. The reaction shows broad substrate scope with products obtained in a highly regioselective manner in good to excellent isolated yields. Mechanistic insights suggest the formation of a Co(III)-aryl key species via a rate-determining arene C-H activation during the annulation reaction.

Non-emissive RuII Polypyridyl Complexes as Efficient and Selective Photosensitizers for the Photooxidation of Benzylamines

Five new RuII polypyridyl complexes bearing N-(arylsulfonyl)-8-amidoquinolate ligands and three of their biscyclometalated IrIII congeners have been prepared and employed as photocatalysts (PCs) in the photooxidation of benzylamines with O2. In particular, the new RuII complexes do not exhibit photoluminescence, rather they harvest visible light efficiently and are very stable in solution under irradiation with blue light. Their non-emissive behavior has been related to the low electrochemical energy gaps and rationalized on the basis of theoretical calculations (DFT analysis) that predict low S0←T1 energy values. Moreover, the RuII complexes, despite being non-emissive, display excellent activities in the selective photocatalytic transformation of benzylamines into the corresponding imines. The presence of an electron-withdrawing group (-CF3) on the arene ring of the N-(arylsulfonyl)-8-amidoquinolate ligand improves the photocatalytic activity of the corresponding photocatalyst. Furthermore, all the experimental evidence, including transient absorption spectroscopy measurements suggest that singlet oxygen is the actual oxidant. The IrIII analogues are considerably more photosensitive and consequently less efficient photosensitizers (PSs).

Cobalt catalyzed electrochemical [4 + 2] annulation for the synthesis of sultams

Cobalt catalyzed electrochemical [4 + 2] annulation of sulfonamides with alkynes is demonstrated in this work, which provided a practical and environmentally friendly way to synthesize structurally diverse sultams. Notably, by employing anodic oxidation in an undivided cell to recycle the cobalt catalyst, this electrochemical method avoided the utilization of stoichiometric amount of metallic oxidant, delivering H2 as the sole by-product. Moreover, this cobalt catalyzed electrochemical protocol proved to be practical and scalable. When the model reaction was scaled up to 5.0 mmol, 86% yield of product could still be obtained.

Rhodium(i)-catalyzed mono-selective C-H alkylation of benzenesulfonamides with terminal alkenes

The Rh(i)-catalyzed ortho-alkylation of benzenesulfonamides with alkenes with the aid of an 8-aminoquinoline directing group is reported. The reaction is applicable to a variety of benzenesulfonamide derivatives and various alkenes. Curiously, unactivated

Metal-Binding Pharmacophore Library Yields the Discovery of a Glyoxalase 1 Inhibitor

Anxiety and depression are common, highly comorbid psychiatric diseases that account for a large proportion of worldwide medical disability. Glyoxalase 1 (GLO1) has been identified as a possible target for the treatment of anxiety and depression. GLO1 is a Zn2+-dependent enzyme that isomerizes a hemithioacetal, formed from glutathione and methylglyoxal, to a lactic acid thioester. To develop active inhibitors of GLO1, fragment-based drug discovery was used to identify fragments that could serve as core scaffolds for lead development. After screening a focused library of metal-binding pharmacophores, 8-(methylsulfonylamino)quinoline (8-MSQ) was identified as a hit. Through computational modeling and synthetic elaboration, a potent GLO1 inhibitor was developed with a novel sulfonamide core pharmacophore. A lead compound was demonstrated to penetrate the blood-brain barrier, elevate levels of methylglyoxal in the brain, and reduce depression-like behavior in mice. These findings provide the basis for GLO1 inhibitors to treat depression and related psychiatric illnesses.

Enhanced Performance of Organic/Inorganic Hybrid Nanomaterials bearing Impregnated [PdL2] Complexes as Counter-Electrode Catalyst for Dye-Sensitized Solar Cells

N-coordinate Pd2+ complexes [PdL2] (L: N-N-quinoline-8-yl-R-benzenesulfonamides) (6–10) and [PdL2] complexes assembled on multi-wall carbon nanotubes (MWCNTs) hybrid nanomaterials were fabricated and characterized by various techniques. The [PdL2] impregnated MWCNTs materials (11–15) were applied as a counter electrode (CE) catalyst for triiodide to iodide reduction reaction in the dye-sensitized solar cells (DSSC) and investigated electro-catalytic activities. The MWCNTs-supported [PdL2] CEs (11–15) are exhibits as Pt-free CE with good power conversion efficiencies (PCEs), and compared to platinum and bare MWCNTs CEs and the PCE of bare MWCNTs was clearly improved by means of [PdL2] complexes (6–10). The DSSCs based on the hybrid counter electrodes (CEs) (11–15) and bare MWCNTs are indicated a relative efficiency (?rel) of 64.27%, 54.07%, 53.75%, 51.52% 44.82% and 27.27% concerning a Pt CE control device set at 100%. The report emphasizes that [PdL2] impregnated MWCNTs type counter electrodes (CEs) (11–15) are promising as effectively catalyst in working device design, particularly taking into account the eco-friendly approach of the hybrids.

Performance improvement of RuII complexes pyridinyl backbone on dye-sensitized solar cells (DSSC)

Two new series of RuII complexes (6–10 bearing an imine bond and 16–20 bearing a sulfonamidate fragment) based 8-aminoquinoline backbone were prepared and characterized by NMR, FT-IR, elemental analysis, UV–vis, CV etc. and tested as a photoact

Aminoquinoline-directed, cobalt-catalyzed carbonylation of sulfonamide sp2 C-H bonds

We report a method for cobalt-catalyzed, aminoquinoline-directed sp2 C-H bond carbonylation of sulfonamides. The reactions proceed in a dichloroethane solvent, and employ diisopropyl azodicarboxylate as a carbon monoxide source, Mn(OAc)2/

Synthesis, in?vitro β-glucuronidase inhibitory potential and molecular docking studies of quinolines

In this study synthesis and β-glucuronidase inhibitory potential of 3/5/8 sulfonamide and 8-sulfonate derivatives of quinoline (1–40) are discussed. Studies reveal that all the synthetic compounds were found to have good inhibitory activity against β-gluc

Cobalt-catalyzed aryl C-H activation and highly regioselective intermolecular annulation of sulfonamides with allenes

Herein we describe a cobalt-catalyzed C-H activation of aryl and heteroaryl sulfonamides and their intermolecular heteroannulation reaction with allenes, providing a convergent strategy for the synthesis of biologically interesting heterocyclic scaffolds. Carbometallation of allenes proceeds selectively through a Co-alkenyl pathway for a wide range of electron-poor and electron-rich allenes.