290-96-0Relevant academic research and scientific papers
MR3-substituted alkynes 2 and 3 (M = Si, Ge, Sn; R = alkyl) show high reactivity in inverse-type Diels-Alder reactions with the re-electron-deficient 1,2,4,5-tetrazine 1 in strict contrast to the corresponding carbon compounds.
Heldmann, Dieter K.,Sauer, Juergen
, p. 5791 - 5794 (1997)
MR3-substituted alkynes 2 and 3 (M = Si, Ge, Sn; R = alkyl) show high reactivity in inverse-type Diels-Alder reactions with the re-electron-deficient 1,2,4,5-tetrazine 1 in strict contrast to the corresponding carbon compounds. Kinetic data prove the huge accelerating effect of the trialkyltin substituent, offering a simple access to new heteroaromatic organotin derivatives, which can be easily transformed by standard methods of organotin chemistry.
4,4′-Bipyridazine: A new twist for the synthesis of coordination polymers
Domasevitch, Konstantin V.,Gural'Skiy, Il'Ya A.,Solntsev, Pavlo V.,Rusanov, Eduard B.,Krautscheid, Harald,Howard, Judith A. K.,Chernega, Alexander N.
, p. 3140 - 3148 (2007)
A new polydentate ligand 4,4′-bipyridazine (4,4′-bpdz) was prepared by employing inverse electron demand cycloaddition of 1,2,4,5-tetrazine. A unique combination of structural simplicity, ampolydentate character and efficient donor properties towards Cu(i), Cu(ii) and Zn(ii) provide wide new possibilities for the synthesis of coordination polymers incorporating the 4,4′-bpdz module either as a bi-, tri- or tetradentate connector between the metal ions. 1D coordination polymers Cu 2(4,4′-bpdz)(CH3CO2)4· 4H2O and Zn(4,4′-bpdz)(NO3)2, and interpenetrated (4,4)-nets in [Cu(4,4′-bpdz)2(H 2O)2]S2O6 were closely related to 4,4′-bipyridine compounds. 1D "ladder-like" polymer Cu 2(4,4′-bpdz)3(CF3CO2) 4 and the unprecedented 3D binodal net ({866 3;83) in [Cu3(4,4′-bpdz) 6(H2O)4](BF4)6· 6H2O were based upon a combination of linear and angular organic bridges. Complex [Cu3(OH)2(4,4′-bpdz) 3(H2O)2CF3CO2 2](CF3CO2)2·2H2O has a "NbO-like" 3D topology incorporating discrete dihydroxotricopper(ii) clusters linked by tri- and tetradentate ligands. The tetradentate function of the 4,4′-bpdz ligand was especially relevant for copper(i) complexes, which adopt layered Cu2X2(4,4′- bpdz) (X = Cl, Br) or 3D chiral framework (X = I) structures based upon infinite (CuX)n chains. The electron deficient character of the ligand was manifested by short anion-π interactions (O-π 3.02-3.20; Cl-π 3.35 A), which may be involved as a factor for controlling the supramolecular structure. The Royal Society of Chemistry.
Metal-organic frameworks exhibiting strong anion-π interactions
Gural'skiy, Il'ya A.,Solntsev, Pavlo V.,Krautscheid, Harald,Domasevitch, Konstantin V.
, p. 4808 - 4810 (2006)
Coordination frameworks of pyridazino[4,5-d]pyridazine reveal a pronounced ability for anion-π interactions. The Royal Society of Chemistry 2006.
Tailoring Dihydroxyphthalazines to Enable Their Stable and Efficient Use in the Catholyte of Aqueous Redox Flow Batteries
Hofmann, Jonas D.,Hong, Longcheng,Janek, Jürgen,Mollenhauer, Doreen,Schmalisch, Sebastian,Schr?der, Daniel,Schwan, Sebastian,Wegner, Hermann A.
, p. 3427 - 3438 (2021/06/14)
To enable cost-efficient stationary energy storage, organic active materials are the subject of current investigations with regard to their application in aqueous redox flow batteries. Especially quinones with their beneficial electrochemical properties and natural abundance pose a promising class of compounds for this challenging endeavor. Yet, there are not many active materials available for the catholyte side to realize solely quinone-based systems. Herein we introduce the novel hydroquinone 5,8-dihydroxy-2,3-phthalazine together with two of its derivatives and propose it as a promising active material for the catholyte side of aqueous redox flow batteries. We systematically investigate the electrochemical properties as well as the structure-property relationship of this class of compounds. The unmodified dihydroxyphthalazine exhibits a favorably high redox potential of 796 mV vs SHE in acidic solution that is competitive with benzoquinone compounds. Moreover, the introduced dihydroxyphthalazines feature a high electron transfer rate surpassing benzoquinone species by almost one order of magnitude. With regard to stable cycling performance, we further achieved a high resilience against detrimental side reactions such as Michael addition by adding methyl substituents to the base structure. Our experimental findings are supported and extended by theoretical considerations in terms of density functional theory calculations. With this combined approach we outline further promising dihydroxyphthalazine-based materials with regard to performance-relevant quantities like redox potential, cycling stability, and water solubility. This study aims to propel further research in the field of quinone-based active materials for the catholyte of future aqueous redox flow batteries.
TDO2 INHIBITORS
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Paragraph 1787, (2017/07/14)
Presently provided are inhibitors of cellularly expressed TDO2 and pharmaceutical compositions thereof, useful for modulating an activity of tryptophan 2, 3 dioxygenase; treating immunosuppression; treating a medical conditions that benefit from the inhibition of tryptophan degradation; enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent; and treating tumor-specific immunosuppression associated with cancer.
INHIBITORS OF POLO-LIKE KINASE
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Page/Page column 315, (2012/04/23)
The present invention provides compounds having a structure according to Formula (I):or a salt or solvate thereof, wherein ring A, U1, U2, U3, R2, R3 and R4 are defined herein. The invention further provides pharmaceutical compositions including the compounds of the invention and methods of making and using the compounds and compositions of the invention, e.g., in the treatment and prevention of various disorders, such as Parkinson's disease.
PTERIDINONES AS INHIBITORS OF POLO - LIKE KINASE
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Page/Page column 142; 143, (2011/07/09)
The present invention provides compounds having a structure according to Formula (I) or a salt or solvate thereof, wherein ring A, X, R1, R2, R3, R4, R5 and R6, are defined herein. The invention further provides pharmaceutical compositions including the compounds of the invention and methods of making and using the compounds and compositions of the invention, e.g., in the treatment and prevention of various disorders, such as Parkinson's disease.
Copper(I) and silver(I) coordination frameworks involving extended bipyridazine bridges
Degtyarenko, Anna S.,Solntsev, Pavlo V.,Krautscheid, Harald,Rusanov, Eduard B.,Chernega, Alexander N.,Domasevitch, Konstantin V.
supporting information; experimental part, p. 1910 - 1918 (2009/02/07)
1,4-(Pyridazin-4-yl)benzene (bpph), a new N-donor tetradentate ligand, was prepared by inverse electron demand cycloaddition reacting 1,4-diethynylbenzene and 1,2,4,5-tetrazine. In combination with Cu(i) and Ag(i) ions, it affords coordination framework topologies that were dominated by assembly of dinuclear metal-pyridazine "secondary building blocks" [M2(μ-pdz) 2] supporting further polymeric connectivity. In structures [Cu 2(bpph)(CH3CN)2{S2O6}] (1) and [Ag6(bpph)3(H2O)6{C 6H4(COO)2}2]C6H 4(COO)2·4H2O (8) interconnection of the dinuclear nodes occurs with anionic dithionate and isophthalate bridges, while [Ag2(bpph){C6H5CO2} 2]·2H2O (7) adopts a linear chain structure incorporating disilver(i) pyridazine units and terminal benzoate anions. [Cu4(bpph)5](BF4)4·4CHCl 3 (2) has a 3D supramolecular structure involving polycatenation of the 2D "bilayer" metal-organic topologies built up of five-connected dinuclear nodes. Frameworks of [Ag(bpph){NO3}]·CHCl 3 (3) and [Ag(bpph){C2F5COO}] (5) exist as 2D square-grids nets supported with sets of tetra- and bidentate bipyridazine bridges, while closely related [Ag4(bpph)3{CF 3COO}4]·CH3CN (4) is a 1D "ladder" polymer. The three-fold interpenetrated 3D diamondoid framework of [Ag4(bpph)3{CH3SO 3}4]·2CHCl3 (6) was based upon more complicated tetranuclear nodes [Ag4(μ-pdz)4(pdz) 2]. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2008.
Trisubstituted heterocyclic compounds and their use as fungicides
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, (2008/06/13)
Compounds of general formula (I): in which:Het represents a five or six membered saturated, partially unsaturated or aromatic ring containing between one and six heteroatoms of the group N, O, S, in which the heterocycle is substituted in an adjacent manner with -P-Q1-T-Q2, -GZ and Y, such that the substituant -GZ is adjacent to both. the other substituants being as defined in the description,process for preparing these compounds,fungicidal compositions comprising these compounds,processes for treating plants by applying these compounds or compositions.
Radical Cations and Anions of 1,2,4,5-Tetrazines: an Electron Spin Resonance and Cyclic Voltammetric Study
Fischer, Hans,Mueller, Thomas,Umminger, Irmgard,Neugebauer, Franz A.,Chandra, Harish,Symons, Martyn C. R.
, p. 413 - 422 (2007/10/02)
Exposure to (60)Co γ-ray of dilute solutions of a range of s-tetrazines in fluorotrichloromethane at 77 K gave the corresponding radical cations, identified by their e.s.r. spectra.Two distinct types of spectra were obtained, one showing large hyperfine coupling to four equivalent (14)N nuclei is assigned to n(?)-radical cations, and the other, only found for -NR2 substituents, with strong coupling to two nitrogen nuclei, is assigned to ?-radical cations.The former include the parent s-tetrazine and the 3,6-dimethyl, -diphenyl, dichloro, dimethoxy, bis(methylthio), and di(aziridin-1-yl) derivatives.The latter were also prepared in fluid solution, and showed reversible behaviour in their cyclic voltammograms, in contrast with the former group.The corresponding radical anions have been studied in both fluid and solid solution, all derivatives showing major hyperfine coupling to the four ring (14)N nuclei.Total spin densities have been estimated for both types of radical cations and for the radical anions, and in all cases the total is in the 1.05-1.2 range.This deviation from unity is interpreted in terms of spin polarisation giving rise to considerable negative spin densities.
