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Synthesis, structure and redox properties of ferrocenylmethyl-nucleobases

Lookup NU author(s): Professor Andrew Houlton, Dr Ashleigh Gibson, Dr Ben Horrocks, Emeritus Professor Bill Clegg, Dr Mark Elsegood

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Abstract

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-C 5H4CH2N(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. © The Royal Society of Chemistry 1999.


Publication metadata

Author(s): Houlton A, Isaac CJ, Gibson AE, Horrocks BR, Clegg W, Elsegood MRJ

Publication type: Article

Publication status: Published

Journal: Journal of the Chemical Society - Dalton Transactions

Year: 1999

Issue: 18

Pages: 3229-3234

Print publication date: 21/09/1999

ISSN (print): 0300-9246

ISSN (electronic):

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/a905168f

DOI: 10.1039/a905168f


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