Modular, step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides

Autor: Buchanan, Helena S., Pauff, Steven M., Kosmidis, Tilemachos D., Taladriz-Sender, Andrea, Rutherford, Olivia I., Hatit, Marine Z. C., Fenner, Sabine, Watson, Allan J. B., Burley, Glenn A.
Přispěvatelé: University of St Andrews. School of Chemistry
Jazyk: angličtina
Rok vydání: 2017
Předmět:
ISSN: 1523-7060
Popis: This work was supported by an EPSRC-GSK industrial CASE studentship for H.B., a University studentship for T.D.K., and postdoctoral funding for S.P. by the Leverhulme Trust (RPG-2014-313). Two Pd-catalyzed methods to access 6-heteroaryl 2-aminopurine ribonucleosides from 6-chloroguanosine are described. First, Pd-132-catalyzed Suzuki–Miyaura cross-coupling using a series of boron substrates and 6-chloroguanosine forms 6-heteroaryl-2-aminopurines in a single step. The versatility of 6-chloroguanosine is further demonstrated using a modified Sonogashira coupling employing potassium iodide as an additive. Finally, the utility of the 6-alkynyl-2-aminopurine ribonucleoside as a dipolarophile in [3 + 2] cycloadditions is presented, affording triazoles and isoxazoles when reacted with azide and isonitrile 1,3-dipoles, respectively. Publisher PDF
Databáze: OpenAIRE