Synthesis, structure and redox properties of ferrocenylmethylnucleobases
| Autor: | Benjamin R. Horrocks, Mark R. J. Elsegood, Andrew Houlton, Christian J. Isaac, AE Gibson, William Clegg |
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| Rok vydání: | 1999 |
| Předmět: | |
| Zdroj: | Journal of the Chemical Society, Dalton Transactions. :3229-3234 |
| ISSN: | 1364-5447 0300-9246 |
| DOI: | 10.1039/a905168f |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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