Arts and Sciences
Pteridines are an important heterocycle often used in the development of pharmaceutically relevant compounds, and in the field of supramolecular chemistry. Their synthetic use is often hampered by the notorious insolubility of pterins, slowing the development of novel pteridine derivatives. Reactions which expedite the rapid development of new pterins are thus of great importance. Through a dual role of diazabicycloundecene (DBU), 7-carboxymethyl-pterin is converted to the soluble DBU salt, with additional DBU promoting an ester-to-amide transformation. We have explored this reaction to assess its scope and identify structural features in the amines which significantly affect success, monitored the reaction using pseudo-first order kinetics, and further adapted the reaction conditions to allow for product formation in as little as 5 min, with yields often >80%.
Bockman, Anna, "Exploring the scope of DBU-promoted amidations of 7-carboxymethyl-pterin" (2020). Symposium on Undergraduate Research and Creative Expression (SOURCE). 884.