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Updated: Aug 9, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Condensation of triformylmethane with guanosine
N Koissi1, K Neuvonen, T Munter
1Department of Chemistry, University of Turku, Finland.
Abstract:
Guanosine has been reacted with triformylmethane (TFM) in refluxing pyridine. Four different products, 4-7, were isolated by preparative RP-HPLC, and characterized by 1H and 13C NMR and UV spectroscopy and mass spectrometry. One of the products. the cyclic 1:1 adduct 4, is a stable cyclic carbinolamine formed probably by cyclization of the expected aminomethylene derivative 3. Compound 4 then undergoes reversible dehydration to the fully conjugated adduct 5. The appearance of the additional adducts, 6 and 7, suggests that TFM is prone to transformations resulting in the formation of methylenemalonaldehyde (9) and 1,1,3,3-tetraformylpropane (11).
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