The Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cadmium

Shirley, D. A.

doi:10.1002/0471264180.or008.02

Cited by 9 publications

(11 citation statements)

References 62 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…aldol [58]-, Diels-Alder [59]-, Heck [60,61]-, Wittig [62] and Grignard [63] reaction. The most common C-C bond formations between aromatic compounds are the Suzuki [64,65], Stille [66] and Ullman [67] reactions.…”

Section: Carbon-carbon Couplingmentioning

confidence: 97%

Asymmetric Oligothiophenes : Chemical Evolution of Multimodal Amyloid Ligands

Johansson

2015

Linköping Studies in Science and Technology. Dissertations

View full text Add to dashboard Cite

Luminescent conjugated polymers (LCPs) and luminescent conjugated oligothiophenes (LCOs) can be used as molecular probes to study diseases associated with protein aggregation. The conventionally used dyes to study and detect protein aggregates, denoted amyloid, have been Congo red (CR) and Thioflavin T (ThT). In contrast to these amyloid ligands, LCOs offer the possibility to detect aggregated proteinaceous species occurring at earlier stages of amyloid formation as well as to distinguish different morphotypes of protein aggregates. The interaction between the LCOs and the protein deposits can be studied by fluorescence spectroscopy and microscopy both in vitro and ex vivo. In this thesis we report the development of multimodal asymmetric LCOs that can be utilized with two novel techniques, Surface Plasmon Resonance (SPR) and Positron Emission Tomography (PET), to study and visualize the interaction between LCO and amyloid fibrils in real time. With SPR, we have been able to determine binding affinities between LCO and amyloid, and with PET we have shown that radiolabelled LCOs might be used as a non-invasive method to study amyloid deposits in vivo. In addition, by alteration of the backbone (change of thiophene units), and of adding different side chain functionalities, we have shown that the properties of the amyloid ligands have a huge impact of the binding to different stages or forms of protein aggregates. By making asymmetrical LCOs, which can be attached to a surface, we also foresee a methodology that will offer the possibility to create a sensitive and selective detection method, and maybe lead to a lab-on-a-chip-application. VIII IX POPULÄRVETENSKAPLIG SAMMANFATTNINGTidigare arbete i Peter Nilssons forskargrupp har visat att luminiscenta konjugerade polymerer (LCPs) och luminiscenta konjugerade oligotiofener (LCOs) kan användas som molekylära prober för att studera sjukdomar associerade till protein aggregering. De konventionellt använda markörerna för att studera och detektera proteinaggregat, så kallad amyloid, är Kongorött (CR) och Thioflavin T (ThT). I kontrast till dessa konventionella markörer har Nilssons forskargrupp visat att LCOs, på grund av deras flexibla konjugerade struktur, och laddning kan upptäcka både tidigare stadier av proteinaggregat samt också skilja på olika typer av aggregat. När LCO interagerar med proteinaggregaten kan denna interaktion studeras med fluorescens mikroskopi både in vitro och ex vivo. Arbetet i den här avhandlingen beskriver utvecklingen av amyloidligander från polymera till osymmetriska material samt två nya tekniker för att studera interaktionen mellan LCO och amyloida fibrer i realtid, Surface Plasmon Resonance (SPR) och Positron Emission Tomography (PET). Med SPR har vi kunnat bestämma bindingsaffiniteter mellan LCO och amyloida fibrer, och med PET har vi visat att radioinmärkta LCOs kan användas som en icke-invasiv metod för att studera amyloid in vivo. Under min forskarutbildning har jag syntetiserat och karaktäriserat både symmetriska och osymmetr...

show abstract

Section: Carbon-carbon Couplingmentioning

confidence: 97%

Asymmetric Oligothiophenes : Chemical Evolution of Multimodal Amyloid Ligands

Johansson

2015

Linköping Studies in Science and Technology. Dissertations

View full text Add to dashboard Cite

show abstract

“…The second stage of the synthesis of our desired molecule was linked to the aziridine ring opening to produce 2-phenylethylamine, which in turn gives rise to isoquinoline derivatives. We used the principles of Gilbert's reaction 13,14 to make the ring opened. The reaction was perfor-med as following: 4-bromo-1,2-dimethoxybromobenzen was added to a medium with tetrahydrofuran anhydrous and magnesium grit, and afterwards 2-methyl-1-tosylaziridine was added to the reagents.…”

Section: Synthesis Of the Desired Compoundmentioning

confidence: 99%

Impact of a Newly Synthesized Molecule (2-chloro-N-(1-(3,4-dimethoxyphenyl) propan-2-yl)-2-phenylacetamide) on the Bioelectrogenesis and the Contractile Activity of Isolated Smooth Muscles

Gledacheva¹,

Stefanova²,

Slavchev³

et al. 2020

View full text Add to dashboard Cite

Introduction: Examination of the potential possibilities of 2-chloro-N-(1-(3,4-dimethoxyphenyl)propan-2-yl)-2-phenylacetamide (IQP) to affect bioelectrogenesis and the contractile activity of isolated smooth muscles (SM) from stomach. Aim: Having in mind the structural similarities between the molecules of papaverine and IQP, the aim of the present study was to examine such features of the newly synthesized molecule that may potentially affect the muscle tonus, spontaneous bioelectrical and contractile activities of smooth muscles isolated from the stomach, basing on specific mechanisms of papaverine. Materials and methods: The synthesis of IQP is based on the initially formed aziridine ring by principles of Gilbert’s reaction. Impact of IQP on the bioelectrogenesis and the contractile activity of isolated smooth muscles from male Wistar rats was measured by the single sucrose-gap method and isometrically recorded. Results: IQP (1×10-5 – 2.5×10-4 mol/l) causes muscle relaxation, producing changes in two processes that have influence on the mechanical activity of smooth muscles:1.    Blocked Ca2+ influx through the potential-dependent membrane Ca2+ channels, followed in turn by lowering the Ca2+ intracellular levels. This effect is proved by the changes in the frequency and amplitude of spike-potentials in sucrose-bridge experiments when IQP is applied.2.    Activation of a cAMP-dependent signal cascade. The relaxing effect of IQP was significantly reduced in the presence of KT5720(5×10-6 mol/l), an inhibitor of protein kinase A. Conclusion: We assume that there might be interconnections between these two IQP-dependent processes, because PKA-dependent phosphorylation of the L-type Ca2+ channels in smooth muscles provokes a reaction of inactivation.

show abstract

“…Oxalyl chloride, as a carbonylated reagent, had been reported to undergo substitution reactions with two equivalents of mono-functionalized organometallic compounds, such as Grignard reagents, and organolithium and organocopper compounds, to form 1,2-disubstituted 1,2-diones [38][39][40][41][42][43]. However, when organodimetallic reagents of these organometallic compounds were used, the reaction frequently led to the formation of complexes, or an inseparable mixture because of over-addition, polymerization or decomposition.…”

Section: Reactions Of Zirconacycles 21 11-cycloaddition Of Oxalyl Dmentioning

confidence: 99%

Zirconacycle-mediated synthesis of carbocycles

Chen

2010

Chin. Sci. Bull.

View full text Add to dashboard Cite

Direct transformation of five-membered zirconacycles to carbocyclic compounds is of great synthetic interest. The reaction of zirconacycles with electrophiles containing at least two reactive functional groups or an oxidant affords various carbocycles through cross coupling, addition, and/or oxidative coupling reactions. In this paper, we present our recent results on the zirconacycle-mediated formation of carbocycles, including: (1) 1,1-cycloaddition of oxalyl dichloride with zirconacycles; (2) benzoquinone-promoted coupling of zirconacyclopentadienes in the presence of CuCl; (3) cycloaddition of zirconacyclopentadienes to quinones; (4) cycloaddition of zirconacyclopentadiene with 2-bromoacrylate, 2-bromoacrylaldehyde and 3-bromofuran-2,5-dione in the presence of CuCl; (5) one-pot coupling of two alkynes and an alkene to form cyclohexene derivatives via zirconacyclopentadienes; and (6) dianionic cycloaddition of decatetraenes with esters or acyl chlorides to form nine-membered carbocycles.

show abstract

The Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cadmium

Cited by 9 publications

References 62 publications

Asymmetric Oligothiophenes : Chemical Evolution of Multimodal Amyloid Ligands

Asymmetric Oligothiophenes : Chemical Evolution of Multimodal Amyloid Ligands

Impact of a Newly Synthesized Molecule (2-chloro-N-(1-(3,4-dimethoxyphenyl) propan-2-yl)-2-phenylacetamide) on the Bioelectrogenesis and the Contractile Activity of Isolated Smooth Muscles

Zirconacycle-mediated synthesis of carbocycles

Contact Info

Product

Resources

About