Aromatensynthese aus 1,2,3‐Selenadiazolen und α‐Pyronen

Meier, Herbert; Molz, Thomas; Merkle, U.; Echter, Toni; Lorch, Margret

doi:10.1002/jlac.198219820511

Cited by 37 publications

(13 citation statements)

References 36 publications

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“…Therefore, we have chosen methyl coumalate (5), which is a commercially available electrophilic diene, as a possible reaction partner for enyne 4. [13] The inverse-electron-demand Diels-Alder reaction took place chemoselectively to afford 6. The modularity of the synthetic routine allows, at this point, the introduction of differently substituted fused aryl rings by utilising other dienes (e.g., 2H-pyran-2-ones or tetrazines) to access a variety of monoarylcyclooctynes.…”

Section: Resultsmentioning

confidence: 99%

A Non‐Fluorinated Monobenzocyclooctyne for Rapid Copper‐Free Click Reactions

Varga

Kállay

Hegyi

et al. 2011

Chemistry A European J

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We designed and synthesised carboxymethylmonobenzocyclooctyne (COMBO) through a four-step reaction pathway. COMBO is a new, structurally simple, non-fluorinated, and directly conjugable copper-free click reagent, which shows excellent reaction kinetics, as also evidenced by theoretical calculations. Additionally, the carboxylic acid appendage allows further conjugation to biomolecules or fluorescent labels. The utility of COMBO in bioorthogonal labelling schemes was demonstrated when a COMBO-containing fluorescent label was employed in glycan imaging of HeLa cells (metabolically modified to have azidosialic acid residues on their cell-surface glycans).

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Section: Resultsmentioning

confidence: 99%

A Non‐Fluorinated Monobenzocyclooctyne for Rapid Copper‐Free Click Reactions

Varga

Kállay

Hegyi

et al. 2011

Chemistry A European J

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“…2 Such units have been found in various natural products as well as in pharmacologically active substances:3, 4 Iprindole ( 1 ),5 the first second‐generation antidepressant (TCA), and jolynamine ( 2 ),6 which was isolated from a dark brown alga belonging to the family Scytosiphonaceae, contain a cycloocta[ b ]indole skeleton (Figure 1). Very limited methods, especially those involving the unfavorable formation of eight‐membered rings, have been developed for the synthesis of these type of products 2b,c,d. 7 Thus, new methodologies for the efficient synthesis of this type of skeleton are highly desired.…”

Section: Methodsmentioning

confidence: 99%

A Sensitive and Selective Fluorescent Probe for Cysteine Based on a New Response‐Assisted Electrostatic Attraction Strategy: The Role of Spatial Charge Configuration

Zhou

Jin

Sun

et al. 2013

Chemistry A European J

101

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A new strategy for fast fluorescent detection of cysteine (Cys), based on a response-assisted electrostatic attraction, is demonstrated. By utilizing this strategy, we designed and synthesized three fluorescent probes for the specific detection of Cys under actual physiological conditions. The probe m-CP, a coumarin fluorophore conjugated with a substituted methyl pyridinium group through an unsaturated ketone unit, showed highly selective and sensitive detection for cysteine (Cys) over homocysteine (Hcy) and glutathione (GSH). The kinetic analysis indicated that the sensing process was highly accelerated (a response time less than 1 min) by the response-assisted electrostatic attraction. More importantly, control experiments with isomeric probes first demonstrated that the spatial charge configuration of the probe played an important role in Cys-preferred selectivity and kinetic rate acceleration. Furthermore, the practical utility of the probe m-CP in the fluorescent labeling of Cys residues within proteins was demonstrated. Finally, these probes were employed in living cell imaging with HeLa cells, in which it displayed satisfactory cell permeability and enabled us to distinguish active thiols in the cytoplasm, nucleus, and mitochondria.

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“…13 C spectra were referenced to residual chloroform at δ 77.0 ppm and the signals are reported as chemical shift (ppm) followed by (in brackets) the peak assignment. Cyclooctyne was prepared according to Meier et al 12 and compounds 19, 20, 22, and 23 were previously reported. 5…”

Section: Methodsmentioning

confidence: 99%

Manifestations of the Alder−Rickert Reaction in the Structures of Bicyclo[2.2.2]octadiene and Bicyclo[2.2.2]octene Derivatives

et al. 2007

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The Alder-Rickert ethylene extrusion reaction manifests in the ground state structures of compounds 9-12 which contain the bicyclo[2.2.2]octadiene moiety and compounds 13, 14, and 17-20 which contain the bicyclo[2.2.2]octene moiety. A significant decrease of the 13C-13C one-bond coupling constants for the C-C bonds, which break in this fragmentation reaction, suggests lengthening, and hence weakening of these bonds. In the unsymmetrical systems these effects are also shown to be associated with strengthening of the CH2-CH2 bond, which is ultimately lost from the molecule as ethylene. Low-temperature crystal structures of compounds 9-12 and 16 provide evidence for similar crystal packing requirements of the CH2-CH2 and CH=CH moieties.

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Aromatensynthese aus 1,2,3‐Selenadiazolen und α‐Pyronen

Cited by 37 publications

References 36 publications

A Non‐Fluorinated Monobenzocyclooctyne for Rapid Copper‐Free Click Reactions

A Non‐Fluorinated Monobenzocyclooctyne for Rapid Copper‐Free Click Reactions

A Sensitive and Selective Fluorescent Probe for Cysteine Based on a New Response‐Assisted Electrostatic Attraction Strategy: The Role of Spatial Charge Configuration

Manifestations of the Alder−Rickert Reaction in the Structures of Bicyclo[2.2.2]octadiene and Bicyclo[2.2.2]octene Derivatives

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