Analysis of thyrostatic heteroaromatic thioamides (review)

Dolinkin, A. O.; Chernov’yants, M. S.

doi:10.1007/s11094-010-0407-8

Cited by 12 publications

(6 citation statements)

References 51 publications

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“…As useful building blocks in biochemistry and pharmacology, 2-substituted 1,4,5,6-tetrahydropyrimidine and 2-imidazoline derivatives attracted a great deal of interest for their potential anthelmintic, antidepressant, antibacterial, and fungicide activity . In particular, many researchers have focused on the catalytic cascade cycloaddition reaction of aromatic nitriles with diamines because it is a direct method for synthesizing imidazoline and tetrahydropyrimidine rings according with the requirements of green chemistry .…”

Section: Resultsmentioning

confidence: 99%

Solvent Templates Induced Porous Metal–Organic Materials: Conformational Isomerism and Catalytic Activity

et al. 2015

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Solvent templates induced Co-based metal-organic materials; conformational isomers {[Co2(pdpa)(CH3CN)(H2O)3]·CH3OH·H2O}n (1) and {[Co2(pdpa)(CH3CN)(H2O)3]}n (2) and {[Co5(pdpa)2(μ3-OH)2(H2O)6]·2H2O}n (3) [H4pdpa = 5,5'-(pentane-1,2-diyl)-bis(oxy)diisophthalic acid] were synthesized under the same solvothermal conditions except with different concentrations of cyclic ethers (1,4-dioxane or tetrahydrofuran) as structure-directing agents. Structural transformations from a three-dimensional (3D) framework of 1 containing channels with dimensions of ∼6 Å × 6 Å to a two-dimensional layer structure of 2 consisting of large open channels with a size of ∼15 Å × 8 Å and then to a 3D nonporous framework of 3, resulting from the different concentrations of cyclic ethers, were observed. The anion-π interactions between electron-efficient oxygen atoms of cyclic ethers and electron-deficient dicarboxylic acid aromatic cores in H4pdpa imported into the synthetic process accounted for the conformational change of the ligand H4pdpa and the following structural variations. A systematic investigation was conducted to explore how different concentrations of structure-directing agents affected the frameworks of resultant metal-organic frameworks. Furthermore, 1-3 were shown to be available heterogeneous catalysts for the synthesis of 2-imidazoline and 1,4,5,6-tetrahydropyrimidine derivatives by the cascade cycloaddition reactions of aromatic nitriles with diamines. The results showed that the catalytic activity of 2 was much higher than that of 1 and 3, because of its unique structural features, including accessible catalytic sites and suitable channel size and shape. In addition, a plausible mechanism for these catalytic reactions was proposed, and the reactivity-structure relationship was further clarified.

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Section: Resultsmentioning

confidence: 99%

Solvent Templates Induced Porous Metal–Organic Materials: Conformational Isomerism and Catalytic Activity

et al. 2015

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“…Imidazolines and their derivatives, as an important class of bioactive molecules, are widely used in the fields of drugs and pharmaceuticals 6. The development of efficient catalyst systems for the synthesis of imidazolines and their derivatives has recently attracted considerable attention.…”

Section: Introductionmentioning

confidence: 99%

Thermally Triggered Solid‐State Single‐Crystal‐to‐Single‐Crystal Structural Transformation Accompanies Property Changes

Ren

Huang

et al. 2015

Chemistry A European J

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The 1D complex [(CuL0.5H2O)⋅H2O]n (1) (H4L = 2,2'-bipyridine-3,3',6,6'-tetracarboxylic acid) undergoes an irreversible thermally triggered single-crystal-to-single-crystal (SCSC) transformation to produce the 3D anhydrous complex [CuL0.5]n (2). This SCSC structural transformation was confirmed by single-crystal X-ray diffraction analysis, thermogravimetric (TG) analysis, powder X-ray diffraction (PXRD) patterns, variable-temperature powder X-ray diffraction (VT-PXRD) patterns, and IR spectroscopy. Structural analyses reveal that in complex 2, though the initial 1D chain is still retained as in complex 1, accompanied with the Cu-bound H2O removed and new O(carboxyl)-Cu bond forming, the coordination geometries around the Cu(II) ions vary from a distorted trigonal bipyramid to a distorted square pyramid. With the drastic structural transition, significant property changes are observed. Magnetic analyses show prominent changes from antiferromagnetism to weak ferromagnetism due to the new formed Cu1-O-C-O-Cu4 bridge. The catalytic results demonstrate that, even though both solid-state materials present high catalytic activity for the synthesis of 2-imidazolines derivatives and can be reused, the activation temperature of complex 1 is higher than that of complex 2. In addition, a possible pathway for the SCSC structural transformations is proposed.

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“…The 2-imidazoline and 2-substituted 1,4,5,6-tetrahydropyrimidine derivatives have often been used for herculean building blocks in molecules with biological and pharmacological activity. − They demonstrate significant activity against several diseases involving inflammation, hyperglycemia, hypercholesterolemia, hypertension, and cancer, and they can also act as antiviral, antidepressant, antibacterial, anthelmintics, and fungicides . The wide requirement for versatile 2-imidazoline and 1,4,5,6-tetrahydropyrimidine derivatives in diverse fields has speeded up the development of different synthetic routes.…”

Section: Introductionmentioning

confidence: 99%

“…The wide requirement for versatile 2-imidazoline and 1,4,5,6-tetrahydropyrimidine derivatives in diverse fields has speeded up the development of different synthetic routes. Among them, the cascade cycloaddition of a nitrile with a diamine that is mediated by various catalysts, which would be a direct approach to synthesis of imidazoline and tetrahydropyrimidine rings in conformity to the guidelines of green chemistry, , has gained especial attention from the academic community. Moreover, a variety of catalysts have also been applied for this purpose, such as H 2 S, , p -toluenesulfonic acid, , sulfur, 1,3-dibromo-5,5-dimethylhydantoin, thioacetamide, and supported 12-tungstophosphoric acid .…”

Section: Introductionmentioning

confidence: 99%

Co(II)/Mn(II)/Cu(II) Coordination Polymers Based on Flexible 5,5′-(hexane-1,6-diyl)-bis(oxy)diisophthalic Acid: Crystal Structures, Magnetic Properties, and Catalytic Activity

Liu

Huang

Zhang

et al. 2015

Crystal Growth & Design

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To systematically explore the impact of coordination complexes on the synthesis of 2-imidazoline and 1,4,5,6-tetrahydropyrimidine derivatives, five Co(II)/Mn(II)/Cu(II) architectures, formulated as {[Co(L)0.5(H2O)2]·CH3OH·H2O} n (1), {[Co(L)0.5(pbib)]·4H2O} n (2), [Mn(L)0.5(Hatz)0.5(H2O)] n (3), {[Cu(L)0.5(phen)2][Cu(L)0.5(phen)2]·0.5L·5H2O} n (4), and {[Cu(L)0.5(2,2′-bpy)(H2O)]·H2O} n (5) (H4L = 5,5′-(hexane-1,6-diyl)-bis(oxy)diisophthalic acid, pbib = 1,4-bis(imidazol-1-ylmethyl)benzene, Hatz = 1H-1,2,4-triazol-3-amine, phen = 1,10-phenanthroline, 2,2′-bipy = 2,2′-bipyridine), have been designed and synthesized. 1 presents a (4,4)-connected 2D sql net with its point (Schläfli) symbol of (44·62)2, which is finally extended to a 3D supramolecular framework by π···π stacking interactions. 2 has a 3D (4,4)-connected new topology net with a point symbol of (86)2. 3 features a (4,4)-connected 3-fold interpenetrating 3D pts topology network with the Schläfli symbol (42·84)2. 4 possesses two binuclear molecules, and these adjacent binuclear units are further stretched to a 2D infinite packing structure through two distinct types of π···π stacking interactions. 5 is a 2D layer structure with the (8)(84·122) topology. The magnetic studies of 1 and 3 elucidate that both of them signify antiferromagnetic interactions. 4 and 5 have been justified to be available heterogeneous catalysts for the synthesis of 2-imidazoline and 1,4,5,6-tetrahydropyrimidine derivatives.

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Analysis of thyrostatic heteroaromatic thioamides (review)

Cited by 12 publications

References 51 publications

Solvent Templates Induced Porous Metal–Organic Materials: Conformational Isomerism and Catalytic Activity

Solvent Templates Induced Porous Metal–Organic Materials: Conformational Isomerism and Catalytic Activity

Thermally Triggered Solid‐State Single‐Crystal‐to‐Single‐Crystal Structural Transformation Accompanies Property Changes

Co(II)/Mn(II)/Cu(II) Coordination Polymers Based on Flexible 5,5′-(hexane-1,6-diyl)-bis(oxy)diisophthalic Acid: Crystal Structures, Magnetic Properties, and Catalytic Activity

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