- Chemistry and dynamics of interaction of nucleosides with pentafluoropyridine
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Interaction of pentafluoropyridine with hydroxyl groups of thymidine, uridine, adenosine, and deoxyadenosine at room temperature leads to the formation of aryl ethers of nucleosides with a high yield. Under severe conditions, one more tetrafluoropyridine residue is attached to pyrimidine fragments of T and U, while purine heterocycle in A remains intact. Nucleoside derivatives are formed with a quantitative yield and can be used in situ as intermediates for, as an example, molecular design of arene analogs of nucleic acids. The reaction with thymidine is a successive-parallel process, the limited stage being arylation of the secondary hydroxyl group. The presence of the vicinal hydroxyl group in pentose results in the opposite rate ratio of the formation of primary and secondary tetrafluoropyridyl ethers of adenine and uridine. Copyright Taylor & Francis, Inc.
- Litvak,Mainagashev,Bukhanets
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- Polynucleotides and their components in the processes of aromatic nucleophilic substitution: I. Chemistry and dynamics of nucleotide arylation with pentafluoropyridine; obtaining of synthons for molecular design of nucleic acid analogues
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Pentafluoropyridine reacts with thymidine, adenosine, and uridine hydroxy groups to give quantitative yields of the corresponding nucleoside di- and triaryl ethers. The nucleophilic substitution reactions proceed successively and in parallel, with the slo
- Litvak,Mainagashev,Bukhanets
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- Oxidative addition of ether O-methyl bonds at a Pt(0) centre
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Pt(PCyp3)2 (Cyp = cyclopentyl) undergoes C-O oxidative addition with 2,3,5,6-tetrafluoro-4-methoxypyridine, pentafluoroanisole, 2,3,5,6-tetrafluoroanisole and 2,3,6-trifluoroanisole yielding platinum methyl derivatives. The reactions occur in preference to C-H or C-F activation.
- Jasim, Naseralla A.,Perutz, Robin N.,Procacci, Barbara,Whitwood, Adrian C.
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supporting information
p. 3914 - 3917
(2014/04/03)
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- Condensation of αβ-unsaturated amines with perfluoroarenes
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Condensation of αβ-unsaturated amines (enamines, keten ON-acetals, ynamines) with perfluoroarenes (perfluorobenzene, perfluorotoluene, bromopentafluorobenzene, perfluoropyridine) leads to the formation of ketones, esters, and amines α-substituted by a perfluoroaryl group. In the case of enamines, C-arylation can be followed by intramolecular N-arylation, giving fluorinated tetrahydrocarbazoles which can then be dehydrogenated by chloranil to give fluorinated carbazoles.
- Blazejewski, Jean-Claude,Wakselman, Claude
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p. 2845 - 2850
(2007/10/02)
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