Nukleophile aromatische Substitution mit 18F-Fluorid an hochsubstituierten Benzolen als Modellverbindungen zur 18F-Markierung von aromatischen Aminosäuren
Final Report Abstract
The project resulted in the following developments which also were published correspondingly: 1. The SNAr is very efficiently applied using the nitro group as the leaving group and the aldehyde group as the auxiliary one which is fast and efficiently removed catalytically. Those conditions facilitate SNAr in high yields even if as electron donating substituents several -OCH3 substituents are present. 2. Contrary to literature as solvent DMF is clearly superior to DMSO and therefore the solvent of choice for SNAr. 3. Since in case of radiofluorinations no acidic protons should be present the use of protecting groups is mandatory. Therefore efficient procedures were tested under the typical radiochemical conditions. 4. As an alternative to substituted benzenes to be radiofluorinated by SNAr , pyridines were studied with substitution patterns resembling situations relevant in tracer developments.
Publications
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Nucleophilic substitution of nitro groups by [18F]fluoride in methoxy-substituted ortho-nitrobenzaldehydes - A systematic study.J.Fluor.Chem., 2009; 130(2): 216-224
Shen B, Loeffler D, Reischl G, Machulla H-J, Zeller K.
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Nucleophilic aromatic substitution by [18F]fluoride at substituted 2-nitropyridines. J.Radioanal.Nucl.Chem. 2010; 283(3): 757-764
Malik N, Solbach C, Voelter W, Machulla H-J.
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Dissertation, Radiofluorinations in Homo- and Heteroaromatic Systems with Application in Two New Types of Metabolic PET-Tracers. 2011
Malik N.
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Mono- and dimethylbenzyls as new protecting groups for no-carrier-added nucleophilic aromaticradiofluorination. J.Radioanal.Nucl.Chem., 2011; 288 (29): 563-569
Malik N, Zlatopolskiy B.D, Solbach C, Voelter W, Reske S.N, Machulla H-J.
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Radiofluorination of 2-fluoropyridines by isotopic exchange with [18F]fluoride. J.Radioanal.Nucl.Chem., 2011; 287(1): 287-292
Malik N, Voelter W, Machulla, H-J, Solbach C.
