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Issue 16, 2005
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Synthesis, characterisation and theoretical calculations of 2,6-diaminopurine etheno derivatives

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Abstract

Four derivatives of 2,6-diaminopurine (1) were synthesised and characterised. When 1 was reacted with chloroacetaldehyde, 5-aminoimidazo[2,1-i]purine (2), 9-aminoimidazo[2,1-b]purine (3), 9-aminoimidazo[1,2-a]purine (4) and diimidazo[2,1-b:2′,1′-i]purine (5) were formed. The purified products (35) were fully characterised by MS, complete NMR assignments as well as fluorescence and UV spectroscopy. The purified, isolated yields of these products (35) varied from 2.5 to 30%. The relative stability of different tautomers was investigated by theoretical calculations. Fluorescence characteristics are also discussed and compared to the starting material 1 and a reference molecule 2-aminopurine.

Graphical abstract: Synthesis, characterisation and theoretical calculations of 2,6-diaminopurine etheno derivatives

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Publication details

The article was received on 20 Apr 2005, accepted on 01 Jun 2005 and first published on 06 Jul 2005


Article type: Paper
DOI: 10.1039/B505508C
Citation: Org. Biomol. Chem., 2005,3, 2924-2929
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    Synthesis, characterisation and theoretical calculations of 2,6-diaminopurine etheno derivatives

    P. Virta, A. Koch, M. U. Roslund, P. Mattjus, E. Kleinpeter, L. Kronberg, R. Sjöholm and K. D. Klika, Org. Biomol. Chem., 2005, 3, 2924
    DOI: 10.1039/B505508C

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