Cycloauration of pyridyl sulfonamides

Abstract

The pyridyl-2-alkylsulfonamides C(5)H(4)N(CH(2))(n)NHSO(2)R (n = 1,2; R = Me, Ph or p-C(6)H(4)Me) and 8-(p-tosylamino)quinoline undergo facile cycloauration reactions with H[AuCl(4)] in water, giving metallacyclic complexes coordinated through the pyridyl (or quinolyl) nitrogen atom and the deprotonated nitrogen of the sulfonamide group. The complexes have been fully characterised by NMR spectroscopy, ESI mass spectrometry and elemental analysis. The X-ray crystal structures of two derivatives reveal the presence of non-planar sulfonamide nitrogen atoms. The complexes show low activity against P388 murine leukaemia cells, possibly as a result of their ease of reduction with mild reducing agents.

Catalytic activity of cycloaurated complexes in the addition of 2‐methylfuran to methyl vinyl ketone

“…Performance of cycloaurated triphenylphosphine sulfide and selenide [9] as catalysts in the addition of 2-methylfuran to MVK Table 4. Performance of N,N -cycloaurated 2-pyridylsulfonamides [8] as catalysts in the addition of 2-methylfuran to MVK The retention times of o-xylene (4.6 min) and 3 (9.6 min) were confirmed by GC analyses of the pure compounds. Known standard solutions of 3 and o-xylene were analysed by GC-MS; A relative response factor of 3: o-xylene was determined to be 1.08 : 1.00 from a series of standard mixtures.…”

“…Therefore the development of air-and moisture-stable gold(III) complexes that can act as catalysts in acid-sensitive reactions is desirable, and some recent studies have been targeted in this area. [7] We have reported the synthesis and characterization of a series of cycloaurated gold(III) complexes derived from pyridyl sulfonamides, [8] phosphine sulfides and triphenylphosphine selenide, [9] and phosphorimines, [10 -12] and wished to assess these complexes as acid-free gold(III) catalyst sources. As a suitable reaction we chose the gold(III)-catalysed addition of 2-methylfuran (1) to methyl vinyl ketone (MVK) (2) to give 4-(5-methyl-2-furanyl)butan-2-one (3) (Scheme 1).…”

Spray coating thin polymeric sensor films for Au3+

“…To further more study the complexation between PSS‐Rho4 and Au 3+ , 1 H NMR experiments were carried out in DMSO‐ d 6 , and the spectra are demonstrated in Figure . In general, chemical shift of sulfonamide N H proton about 6–8 ppm and protons attached to nitrogen atoms may be exchangeable . For free PSS‐Rho4 , there was no chemical shift of the sulfonamine N H protons, which might be attributed to the quick exchange with the residual water in the deuteration solution and increased intermolecular hydrogen bonding of polymer, whereas in the presence of Au 3+ ions, it was appeared and shifted downfield (9.62 ppm).…”

Understanding the microcrystal tests of three related phenethylamines: theortho-metallated (±)-amphetamine formed with gold(III) chloride, and the tetrachloridoaurate(III) salts of (+)-methamphetamine and (±)-ephedrine

“…The Mack structure also shows the trans influence. Kilpin & Henderson (2009), Parish et al (1996) and Vicente et al (1984) have studied these five-membered C,N-chelated dichlorido cycloaurate(III) systems extensively. Damp(AuCl 2 ) and a large number of structural analogues have been studied for their antitumor and antimicrobial properties, with results comparable to cisplatin in vitro and modest results in vivo (Parish et al, 1996).…”