Macrocyclization of cyclic thiosemicarbazones with mercury salts

Blanco, María-Jesús; López‐Torres, Elena; Mendiola, M. Antonia; Brunet, Ernesto; Sevilla, Ma Teresa

doi:10.1016/s0040-4020(02)00016-9

Cited by 34 publications

(18 citation statements)

References 28 publications

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“…Formation of a cyclised intermediate was also observed by Mendiola et al [76] In the presence of copper(II) the tri-A C H T U N G T R E N N U N G azine thione 60 was converted to a macrocycle 65 in 2 h (Scheme 25). The authors picture 65 as in Scheme 25; that is, as a head-to-tail dimer of the mono(thiosemicarbazone) 61 (R = H), but they only report elemental analysis, IR and NMR data.…”

Section: Wwwchemeurjorgsupporting

confidence: 63%

Ligands for Molecular Imaging: The Synthesis of Bis(thiosemicarbazone) Ligands

Christlieb

Dilworth

2006

Chemistry A European J

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Bis(thiosemicarbazones) have been of interest to chemists for over fifty years; they display antitumour, antibiotic and antiviral properties. Recently it has become apparent that they may also provide a convenient way of labelling biologically active molecules by using metallic radionuclides and/or fluorescence. Although apparently simple, the synthesis of bis(thiosemicarbazone) ligands can be problematic. This article provides a summary of the published literature, based on the synthetic strategies used and indicates some of the difficulties that may arise.

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Section: Wwwchemeurjorgsupporting

confidence: 63%

Ligands for Molecular Imaging: The Synthesis of Bis(thiosemicarbazone) Ligands

Christlieb

Dilworth

2006

Chemistry A European J

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“…The Hg(II) complex showed a cathodic peak at -0.33 V, believed to the Hg(II)/Hg(I) process. 18 In conclusion, we prepared two blue, luminescent Zn(II) and Hg(II) chloride complexes with dmasp ligands. The complexes were stabilized from π-π interactions between the par- allel dmasp ligands in the solid state.…”

Section: Resultsmentioning

confidence: 93%

Blue Luminescent Zn(II) and Hg(II) Complexes with 2-[4-(Dimethylamino)styryl]pyridine; Structural and Luminescent Properties

Seo¹,

Ryu²,

Nam³

et al. 2009

Bulletin of the Korean Chemical Society

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Luminescent organic and metal coordination compounds have attracted considerable attention for their potential applications in electroluminescent displays.1 Among coordination compounds, chelate d 10 metal complexes are of great interest due to their high thermal stability and low cost as well as their good photoluminescent and electroluminescent properties. ) complexes with 2-[4-(dimethylamino)styryl] pyridine (dmasp) were prepared and their structural and luminescent properties were investigated. The dmasp ligand was of interest as it had an electron push-pull system, thereby stabilizing the π* levels and, in them, ILCT transitions could arise readily through a conjugated π system, which is also important to ILCT photoluminescent materials as well as the second-order nonlinear optical (NLO) materials. 6 Experimental Synthesis of Zn(dmasp)2Cl2 (1).To a stirred solution of 2-[4-(dimethylamino)styryl]prydine (449 mg, 2.0 mmol) in methanol (15 mL) was added with a solution of ZnCl2 (272 mg, 2.0 mmol) in methanol (5 mL). The reaction mixture was stirred for 12 hr at room temperature. After filtering, the yellow precipitate was collected. Light yellow crystals of 1 were obtained by slow evaporation in a dichloromethane solution. as an internal reference. The absorption (UV-Vis) and photoluminescence (PL) spectra were measured by a Jasco V-570 UV-Vis spectrophotometer and a Hitachi F-4500 fluorescence spectrophotometer, respectively, from 200 to 800 nm. Cyclic voltammetry (CV) experiments were performed on a Bioanalytical Systems CV-50W voltammetric analyzer in a 0.1 M solution of tetrabutylammonium tetrafluoroborate (Bu4NBF4). The Pt disk electrode, Ag/AgNO3 (0.1 M) electrode and Pt electrode were used as the working, reference and counter electrodes, respectively, at a scan rate of 100 mV/s, and ferrocene was used as a reference. Thermal analyses were carried out on a Metler Toledo TGA/DTA 815 analyzer under a nitrogen atmosphere at a heating rate of 10 o C/min. Crystallography. X-ray intensity data were collected at room temperature on a Bruker SMART APEX-II CCD diffractometer using graphite monochromated Mo Kα radiation (λ = 0.71073 Å). Structure was solved by applying the direct method using a SHELXS-97 and refined by a full-matrix least-squares calculation on F 2 using SHELXL-97. All non-hydrogen atoms were refined anisotropically. All hydrogen atoms were placed in ideal positions and were riding on their respective carbon atoms (Biso = 1.2 Beq and 1.5 Beq). Crystal data for 1: C30H32Cl2 N4Zn, Mw = 584.87, Monoclinic, P21/n, a = 14.108 (2)

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“…When dione 139a is an asymmetrical compound the reaction often leads to a mixture of regioisomeric triazines. Also, reactions of semicarbazide 141a or thiosemicarbazide 141b with 139a afford the corresponding 1,2,4-triazin-3-ones 103 or 3-thiones 107 [247] (Scheme 20.41). Furthermore, the reaction of compounds 141 with monosubstituted glyoxal oxime 139b (R 5 ¼ H) is a suitable method to obtain 6-substituted-1,2,4-triazin-3-ones 103 (R 5 ¼ H) and 3-thiones 107 (R 5 ¼ H) [248].…”

Section: From Other Heterocyclesmentioning

confidence: 99%