Issue 1, 2002

Condensation of triformylmethane with adenosine: novel cyclic adducts derived from 1,3-dicarbonyl compounds

Abstract

Condensation of triformylmethane (TFM) with adenosine has been studied in pyridine and aqueous dioxane. One 1 ∶ 1 (2) and two 2 ∶ 1 (6 and 7) TFM–adenosine adducts were isolated. The structural assignment of these products by 1H and 13C NMR and UV spectroscopy and MS spectrometry suggested that the appearance of the 2 ∶ 1 adducts is connected to a competitive self-condensation of TFM, the stable end product of which is benzene-1,3,5-tricarbaldehyde. The intermediates on the reaction pathway can be reacted with adenosine affording a new procedure for nucleic acid base modification. The mechanisms of formation and the role of intramolecular hydrogen bonding in stabilization of cyclic adenosine adducts are discussed.

Graphical abstract: Condensation of triformylmethane with adenosine: novel cyclic adducts derived from 1,3-dicarbonyl compounds

Article information

Article type
Paper
Submitted
31 May 2001
Accepted
26 Oct 2001
First published
30 Nov 2001

J. Chem. Soc., Perkin Trans. 2, 2002, 173-177

Condensation of triformylmethane with adenosine: novel cyclic adducts derived from 1,3-dicarbonyl compounds

K. Neuvonen, N. Koissi and H. Lönnberg, J. Chem. Soc., Perkin Trans. 2, 2002, 173 DOI: 10.1039/B104790F

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