Rapid synthesis of aliphatic amides by reaction of carboxylic acids, Grignard reagent and amines: application to the preparation of [11C]amides

Aubert, C.; Huard‐Perrio, C.; Lasne, Marie‐Claire

doi:10.1039/a702897k

Cited by 29 publications

(19 citation statements)

References 28 publications

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“…Heating the magnesium carboxylate intermediates in the presence of primary or secondary amines has been reported to produce the corresponding [ 11 C]carboxyamides. 25 The product amides have also been subsequently reduced in the presence of sodium borohydride, giving access to [ 11 C]tertiary amines. 26 More indirectly, carboxylation can be followed by activation using reagents such as thionyl chloride or phthaloyl dichloride to prepare active acylation intermediates such as [ 11 C]acetyl and [ 11 C]propionyl chloride.…”

Section: [11c]co2 Fixation By Basic Organometallic Reagentsmentioning

confidence: 99%

11CO2 fixation: a renaissance in PET radiochemistry

et al. 2013

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Carbon-11 labelled carbon dioxide is the cyclotron-generated feedstock reagent for most positron emission tomography (PET) tracers using this radionuclide. Most carbon-11 labels, however, are installed using derivative reagents generated from [11C]CO2. In recent years, [11C]CO2 has seen a revival in applications for the direct incorporation of carbon-11 into functional groups such as ureas, carbamates, oxazolidinones, carboxylic acids, esters, and amides. This review summarizes classical [11C]CO2 fixation strategies using organometallic reagents and then focuses on newly developed methods that employ strong organic bases to reversibly capture [11C]CO2 into solution, thereby enabling highly functionalized labelled compounds to be prepared. Reactions and radiopharmaceuticals that have been translated to the clinic are highlighted.

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Section: [11c]co2 Fixation By Basic Organometallic Reagentsmentioning

confidence: 99%

11CO2 fixation: a renaissance in PET radiochemistry

et al. 2013

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“…11 C]Carboxymagnesiumhalogeniden wurde beschrieben; [134,135] die Reaktion wurde durch Mikrowellenbestrahlung beschleunigt (Schema 28). [136] Mög- Synthese von PET-Tracern Angewandte Chemie führen des "nichtnatürlichen" Fluoratoms kann unbekannte Auswirkungen auf die biologischen Eigenschaften eines Moleküls haben, [143] und es ist schwierig, einen direkten Vergleich zwischen den biologischen Eigenschaften der nichtfluorierten Stammmoleküle, die möglicherweise im Detail bekannt sind, und dem 18 F-markierten Derivat anzustellen.…”

Section: Bei Den Stille-kreuzkupplungen Mit [unclassified

Synthese von ¹¹C‐, ¹⁸F‐, ¹⁵O‐ und ¹³N‐Radiotracern für die Positronenemissionstomographie

et al. 2008

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Die Positronenemissionstomographie (PET) ist eine leistungsfähige Bildgebungsmethode, die zur Untersuchung und Visualisierung der menschlichen Physiologie eingesetzt wird. Das Funktionsprinzip der PET beruht auf der Detektion positronenemittierender Radiopharmazeutika. Aus PET‐Experimenten können direkte Informationen über Stoffwechselvorgänge, Rezeptor‐Enzym‐Funktionen und biochemische Mechanismen im lebenden Gewebe erhalten werden. Anders als die Magnetresonanztomographie (MRT) und die Computertomographie (CT), die in erster Linie anatomische Bilder liefern, kann die PET chemische Veränderungen messen, die bereits vor dem Auftreten anatomischer Krankheitszeichen auftreten. Die PET ist dabei, sich als eine revolutionäre Methode für die Diagnostik von Körperfunktionen zu etablieren, die die Anwendung individueller, auf den Patienten zugeschnittener Behandlungsmethoden ermöglicht. Allerdings ist die Entwicklung von Synthesestrategien für neuartige positronenemittierende Moleküle nicht trivial. In diesem Aufsatz diskutieren wir die entscheidenden Aspekte bei der Synthese von PET‐Radiotracern mit den kurzlebigen Positronenemittern 11C, 18F, 15O und 13N. Der Schwerpunkt liegt auf den jüngsten Fortschritten bei der Entwicklung von Radiomarkierungsstrategien. Wir hoffen, dass dieser Aufsatz das Interesse von Synthesechemikern auch außerhalb der Radiochemie finden wird und die Bedeutung der PET in der molekularen Bildgebung sowie den Bedarf an neuen, innovativen chemischen Strategien für verbesserte Radiomarkierungstechniken aufzeigt.

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“…Belonging to this category of reactions, the synthesis of nocarrier-added (NCA) aromatic and aliphatic [carbonyl-11 C]amides has been reported [185,186]. Thus, both aromatic and aliphatic NCA [carbonyl-11 C]amides were successfully synthesized by the direct coupling of NCA [ 11 C]carboxymagnesium halides, generated in situ, with primary amines.…”

Section: B 11 C-grignard Reagentsmentioning

confidence: 99%

State of Art in 11C Labelled Radiotracers Synthesis

Allard

Fouquet

James

et al. 2008

CMC

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Positron Emission Tomography has become a powerful scientific and clinical tool probing biochemical processes in the human body. Their clinical applications have proven to be vital in the evaluation and diagnosis of diseases. This is due, in large part, to advances in instrumentation and synthetic chemistry. Carbon-11 is a valuable radionuclide in PET as it virtually permits the synthesis of radiolabelled versions of any compound of interest. The syntheses with carbon-11 present several features: limited number of labelled precursors, sub-micromolar amounts of the starting materials, and a need for the introduction of the radioisotope as late as possible in the synthesis. All of these reasons have restricted complex radiosyntheses. The short half-life of carbon-11 (20.4 min) requires the rapid preparation and purification of carbon-11 labelled molecules. Those have to be carried out immediately before use from cyclotron produced precursors ([11C]CO2, [11C]CO, [11C]CH4) or reagents rapidly prepared from them ([11C]CH3I, [11C]COCl2, [11C]HCN). As a consequence carbon-11 has been underused compared to fluorine-18. However, because of the increasing molecular complexity and diversity of biologically active compounds, there is a need for new methodologies giving access in short time and high yield to radioactive (11)C-probes. The aim of this review is to emphasize the methodologies used in this field and to give a comprehensive overview of the numerous advances, which occurred over the past decade. In addition, for each labelling technique or reaction reported, a special attention has been brought to classify the applications in function of the targeted medical domain.

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Rapid synthesis of aliphatic amides by reaction of carboxylic acids, Grignard reagent and amines: application to the preparation of [11C]amides

Cited by 29 publications

References 28 publications

11CO2 fixation: a renaissance in PET radiochemistry

11CO2 fixation: a renaissance in PET radiochemistry

Synthese von ¹¹C‐, ¹⁸F‐, ¹⁵O‐ und ¹³N‐Radiotracern für die Positronenemissionstomographie

State of Art in 11C Labelled Radiotracers Synthesis

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Rapid synthesis of aliphatic amides by reaction of carboxylic acids, Grignard reagent and amines: application to the preparation of [11C]amides

Cited by 29 publications

References 28 publications

11CO2 fixation: a renaissance in PET radiochemistry

11CO2 fixation: a renaissance in PET radiochemistry

Synthese von 11C‐, 18F‐, 15O‐ und 13N‐Radiotracern für die Positronenemissionstomographie

State of Art in 11C Labelled Radiotracers Synthesis

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Product

Resources

About

Synthese von ¹¹C‐, ¹⁸F‐, ¹⁵O‐ und ¹³N‐Radiotracern für die Positronenemissionstomographie