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. 2017 Feb 14;53(14):2226-2229.
doi: 10.1039/c6cc07722f.

Benzimidazopurine nucleosides from N6-aryl adenosine derivatives by PhI(OAc)2-mediated C-N bond formation, no metal needed

Sakilam Satishkumar  1 , Mahesh K Lakshman  2
Affiliations

Benzimidazopurine nucleosides from N6-aryl adenosine derivatives by PhI(OAc)2-mediated C-N bond formation, no metal needed

Sakilam Satishkumar et al. Chem Commun (Camb). .

Abstract

The reaction of a variety of N6-aryl 2'-deoxyadenosine and adenosine derivatives with PhI(OAc)2 in 1,1,1,3,3,3-hexafluoro-2-propanol provides a facile access to benzimidazopurine nucleoside analogues by metal-free C-N bond formation with a purinyl nitrogen atom. These reactions likely proceed via radical-cation/radical processes as indicated by radical inhibition experiments.

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Figures

Figure 1
Figure 1
Reaction times and product yields from the cyclization reactions (the new bond formed is shown with a solid line). a Yield from a 0.9 mmol reaction.
Figure 2
Figure 2
Fluorescence of the eleven compounds (1 mg mL−1 in CH2Cl2) under a 365 nm UV lamp.
Scheme 1
Scheme 1
Initial test of a C–N bond formation in comparison to a known result (the new bond formed is shown with a solid line).
Scheme 2
Scheme 2
Plausible mechanistic courses for the transformation via radical intermediates.
See this image and copyright information in PMC

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