One-pot protocol for N-alkylation of purine, pyrimidine and azole derivatives via alcohols using Ph 3 P/I 2 : simple route for carboacyclic nucleoside synthesis

New reactions that convert alcohols into important classes of compounds are becoming increasingly important as their development contributes to the conservation of our fossil carbon feedstock and the reduction of CO emissions. Two key catalytic alcohol conversion concepts are borrowing hydrogen or hydrogen autotransfer and acceptorless dehydrogenative condensation. Herein, we combined both concepts to synthesize meta-functionalized pyridines. First, diols and amines were linked to β-amino alcohols, which can then undergo a selective dehydrogenative heterocondensation with γ-amino alcohols. Iridium catalysts stabilized by PN P pincer ligands that were developed in our laboratory mediate the reactions most efficiently. All of the 3-aminopyridines that we describe in this paper have been synthesized for the first time, emphasizing the degree of innovation of this method and the problems associated with the synthesis of such meta-functionalized pyridines.

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One-pot protocol for N-alkylation of purine, pyrimidine and azole derivatives via alcohols using Ph 3 P/I 2 : simple route for carboacyclic nucleoside synthesis

Cited by 14 publications

References 35 publications

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N,N‐Dimethylformamide andN,N‐Dimethylacetamide as Carbon, Hydrogen, Nitrogen, and/or Oxygen Sources

Synthese meta‐funktionalisierter Pyridine über selektive dehydrierende Heterokondensation von β‐ und γ‐Aminoalkoholen

Synthesis of meta‐Functionalized Pyridines by Selective Dehydrogenative Heterocondensation of β‐ and γ‐Amino Alcohols

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