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Synthesis, structure and redox properties of ferrocenylmethylnucleobases

1999; Royal Society of Chemistry; Issue: 18 Linguagem: Inglês

10.1039/a905168f

2050-5671

Andrew Houlton, C.J. Isaac, Ashleigh E. Gibson, Benjamin R. Horrocks, W. Clegg, M.R.J. Elsegood,

Metal complexes synthesis and properties

Ferrocenyl derivatives of thymine 1, cytosine 2, and uracil and of N2-acetylguanine and 2-amino-6-chloropurine have been prepared from reactions of [Fe(η5-C5H5)(η5-C5H4CH2N(CH3)3)] I with the corresponding pyrimidine or purine base. The predominant site of alkylation for thymine and cytosine was N1 while for uracil N3 was preferred. Alkylation of the guanine precursor 2-amino-6-chloropurine yielded two products, the N2-monosubstituted, and the N2,N9-disubstituted, derivatives. Acetyl protection/deprotection of the N2 amino group allowed selective N9-alkylation to yield 2-amino-6-chloro-9-ferrocenylmethylpurine. With N2-acetylguanine alkylation occurred at either the N7 or N9 positions in a ≈3∶1 ratio. The structures of eight compounds were determined by single crystal X-ray analysis. Electrochemical investigations by cyclic voltammetry revealed reversible redox processes for the compounds.