Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, N.I.H., Extramural, Nature (London, United Kingdom) called Concerted nucleophilic aromatic substitution with 19F- and 18F-, Author is Neumann, Constanze N.; Hooker, Jacob M.; Ritter, Tobias, which mentions a compound: 1228185-09-8, SMILESS is CC(C1=C([N+]2=C(Cl)N(C3=C(C(C)C)C=CC=C3C(C)C)C=C2)C(C(C)C)=CC=C1)C.[Cl-], Molecular C27H36Cl2N2, Formula: C27H36Cl2N2.
Nucleophilic aromatic substitution (SNAr) is widely used by organic chemists to functionalize aromatic mols., and it is the most commonly used method to generate arenes that contain 18F for use in positron-emission tomog. (PET) imaging. A wide range of nucleophiles exhibit SNAr reactivity, and the operational simplicity of the reaction means that the transformation can be conducted reliably and on large scales. During SNAr, attack of a nucleophile at a carbon atom bearing a ‘leaving group’ leads to a neg. charged intermediate called a Meisenheimer complex. Only arenes with electron-withdrawing substituents can sufficiently stabilize the resulting build-up of neg. charge during Meisenheimer complex formation, limiting the scope of SNAr reactions: the most common SNAr substrates contain strong π-acceptors in the ortho and/or para position(s). Here we present an unusual concerted nucleophilic aromatic substitution reaction (CSNAr) that is not limited to electron-poor arenes, because it does not proceed via a Meisenheimer intermediate. We show a phenol deoxyfluorination reaction for which CSNAr is favored over a stepwise displacement. Mechanistic insights enabled us to develop a functional-group-tolerant 18F-deoxyfluorination reaction of phenols, which can be used to synthesize 18F-PET probes. Selective 18F introduction, without the need for the common, but cumbersome, azeotropic drying of 18F, can now be accomplished from phenols as starting materials, and provides access to 18F-labeled compounds not accessible through conventional chem.
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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics