Organic & Biomolecular Chemistry 2012-11-28

Divergent synthesis of novel 9-deazaxanthine derivatives via late-stage cross-coupling reactions.

Francesca Bartoccini, Giovanni Piersanti, Marco Mor, Giorgio Tarzia, Patrizia Minetti, Walter Cabri

Index: Org. Biomol. Chem. 10(44) , 8860-7, (2012)

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Abstract

A small library of 8-substituted 9-deazaxanthines has been prepared by late-stage diversification of an 8-bromo-9-deazaxanthine. By utilizing palladium-catalyzed cross-coupling reactions a single key precursor can be transformed into a variety of 8-substituted-9-deazaxanthine compounds. Three key 8-bromo-9-deazaxanthine intermediates were efficiently prepared from commercially available 6-chlorouracil in six steps.