Modular,step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides
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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.
Buchanan , H S , Pauff , S M , Kosmidis , T D , Taladriz-Sender , A , Rutherford , O I , Hatit , M Z C , Fenner , S , Watson , A J B & Burley , G A 2017 , ' Modular,step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides ' Organic Letters , vol 19 , no. 14 , pp. 3759-3762 . DOI: 10.1021/acs.orglett.7b01602
© 2017 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
DescriptionThis 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).
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