Exploring structural and conformational behaviour of cyclophanes incorporating imidazole-2-thiones

Mageed, Ahmed Hassoon; Skelton, Brian W.; Sobolev, Alexandre N.; Baker, Murray V.

doi:10.1016/j.tet.2018.04.074

Cited by 9 publications

(17 citation statements)

References 27 publications

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“…The diminished carbon‐chalcogen bond order of 3a / 3b (vs. v ) can be rationalized by the poor overlap of C(2p) and S(3p) orbitals. [ 8 ] This also accounts for the higher reactivity of thioketones compared to ketones in general.…”

Section: Resultsmentioning

confidence: 99%

“…NHTs (NHTs = N‐heterocyclic thiones) such as imidazolin‐2‐thiones can be viewed as the sulfur adducts of NHCs (NHCs = N‐heterocyclic carbenes) and have been extensively used as S‐donors. [ 8 ] The strong interest in NHTs partially roots in the fact that they can be conveniently accessed by reacting well‐established NHCs [ 9 ] with elemental sulfur. As such, odorous and toxic organosulfur compounds ( e.g.…”

Section: Introductionmentioning

confidence: 99%

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Symmetrical and Non‐symmetrical Pd (II) Pincer Complexes Bearing Mesoionic N‐heterocyclic Thiones: Synthesis, Characterizations and Catalytic Properties

Yan

Zhang

et al. 2020

Applied Organom Chemis

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In contrast to well‐established symmetrical pincer complexes, non‐symmetrical metal pincers with the loss of C2v symmetry are much less studied. In this work, mesoionic NHTs (NHTs = N‐heterocyclic thiones), which can be viewed as the sulfur adducts of mesoionic carbenes, are incorporated into pincer complexes for the first time. Two symmetrical and non‐symmetrical phenylene‐bridged bis (NHT) compounds 3a/3b were synthesized as proligands via a “cycloaddition‐alkylation‐thionation” reaction sequence. In a case to access bis (NHT) compound 3c, N‐dealkylation reactions occurred. The carbene NMR signals of NHTs are only partially correlated to the π‐accepting abilities of carbenes, which is different from Bertrand's carbene‐phosphinidene system. The structural analysis of 3a/3b indicates that they possess C‐S partial double bonds. 3a and 3b served as the precursors to access two aryl anion‐linked [SCS/S′] pincer complexes 6a/6b. An external base proved to be essential for this cyclopalladation process. The catalytic properties of 6a/6b in the cycloisomerizations of alkynoic acids have been examined. Finally, non‐symmetrical complex 6a shows superior catalytic performance in such transformations contrasting to its symmetrical counterpart 6b.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Symmetrical and Non‐symmetrical Pd (II) Pincer Complexes Bearing Mesoionic N‐heterocyclic Thiones: Synthesis, Characterizations and Catalytic Properties

Yan

Zhang

et al. 2020

Applied Organom Chemis

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“…Mageed et al [ 22 ] described the synthesis of new cyclophanes 25 – 28 ( Figure 7 ) containing two imidazole-2-thione moieties linked by two xylylene groups by the reaction of imidazolium-linked cyclophanes with sulphur in the presence of K 2 CO 3 and using methanol as solvent. Structures of the new cyclophanes were confirmed and investigated by NMR spectroscopy, as well as by X-ray diffraction studies.…”

Section: Synthesis Of Imidazolic Macrocyclesmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Insights on the Synthesis of N-Heterocycles Containing Macrocycles and Their Complexion and Biological Properties

et al. 2022

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Macrocyclic chemistry has been extensively developed over the past several decades. In fact, the architecture of new macrocyclic models has undergone exponential growth to offer molecules with specific properties. In this context, an attempt is made in this study to provide an overview of some synthetic methods allowing the elaboration of N-heterocycles containing macrocycles (imidazole, triazole, tetrazole, and pyrazole), as well as their applications in the complexation of metal cations or as pharmacological agents.

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“…Imidazole derivatives are an important class of heterocyclic compounds [19,20] that exhibiting biological and pharmacological properties [21][22][23]. Also, oxazocine heterocyclic compounds are active compounds against CNS disorders and are used for the treatment of pain and/or inflammation [24].…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Novel Furochromone and Oxazocine Derivatives as Promising Antitumor Agents with Their Molecular Docking Studies

Borik

2020

Journal of Chemistry

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One-pot efficient synthesis of novel chromone derivatives 4a–h and that of 5a–h were described in a simple method via four-component reaction between furochromone carbaldehyde, amine, isocyanate derivatives, and benzoic acid derivatives or nicotinic acid, respectively. Also, oxazocine derivatives 7a, b were prepared via reaction of visnagine carbaldehyde, ethyl acetoacetate and isocyanate derivatives 2a, b. The obtained derivatives of novel furochromone and oxazocine derivatives were evaluated as promising antitumor agents against panel of two human cell lines, hepatocellular carcinoma (HEPG2) and breast carcinoma (MCF7). The antitumor results suggested that furochromone derivatives 5a–h have activity against MCF7 in comparison with doxorubicin as the standard drug. Furthermore, the molecular docking studies of these novel derivatives of furochromone and oxazocine showed good agreement with the biological results when their binding pattern and affinity towards the active site of EGFR was investigate.

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Exploring structural and conformational behaviour of cyclophanes incorporating imidazole-2-thiones

Cited by 9 publications

References 27 publications

Symmetrical and Non‐symmetrical Pd (II) Pincer Complexes Bearing Mesoionic N‐heterocyclic Thiones: Synthesis, Characterizations and Catalytic Properties

Symmetrical and Non‐symmetrical Pd (II) Pincer Complexes Bearing Mesoionic N‐heterocyclic Thiones: Synthesis, Characterizations and Catalytic Properties

Insights on the Synthesis of N-Heterocycles Containing Macrocycles and Their Complexion and Biological Properties

One-Pot Synthesis of Novel Furochromone and Oxazocine Derivatives as Promising Antitumor Agents with Their Molecular Docking Studies

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