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Improved conditions for a direct and regioselective synthesis of 8-carboxyethyl-7-deazaguanine

Research paper by Jeff M. Pruet, Ilia Kevlishvili

Indexed on: 22 Mar '17Published on: 19 Mar '17Published in: Tetrahedron Letters



Abstract

As deazaguanines have a broad range of applications, from medicinal research to supramolecular assemblies, simple pathways to functionalizable versions of this heterocycle are of noted importance. The cyclization reaction leading to deazaguanines is known to also lead to a furano-isomer, exclusively in some cases. 8-carboxyethyl-7-deazaguanine (1) had failed to form through the typical cyclization conditions and previously required a considerably more longwinded synthetic approach to form over the furo-isomer (2). We report herein a more direct, simplified approach to 1 by iterative modification of the cyclization reaction conditions, which resulted in a complete reversal of regiochemistry in favor of the desired deazaguanine

Graphical abstract 10.1016/j.tetlet.2017.03.055.jpg
Figure 10.1016/j.tetlet.2017.03.055.0.jpg
Figure 10.1016/j.tetlet.2017.03.055.1.jpg
Figure 10.1016/j.tetlet.2017.03.055.2.jpg