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.