Beilstein J. Org. Chem.2021,17, 193–202, doi:10.3762/bjoc.17.19
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Keywords: Arbuzov reaction; 2,6-bistriazolylpurines; nucleophilic aromatic substitution; purinylphosphonates; Introduction
Acyclic nucleoside phosphonates (ANPs) are an important compound class due to their biological activity profile [1][2][3][4][5][6]. Compounds bearing a phosphonate moiety in their N9
: DMSO-d6, 90 °C.
Single-crystal X-ray analysis of diethyl (9-heptyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)-9H-purin-6-yl)phosphonate (4d). CCDC-2044976.
Structural diversity and synthetic methods of purinylphosphonates. MWI = microwave irradiation; LG = leaving group.
Synthetic routes for the formation of
purinylphosphonates 4.
Synthesis of phosphonates 2, 7, and 8.
Synthesis of phosphonic acid monoesters 3 and 7–9 as well as phosphonic acid 10.
Synthesis of 2,6-bistriazolylpurine derivatives 6a–i.
SNAr–Arbuzov reaction between the bistriazolylpurines 6a–i and P(OEt)3.
Synthesis of 2,6-bistriazolylpurines 6a–i (5→6a–i
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Graphical Abstract
Scheme 1:
Structural diversity and synthetic methods of purinylphosphonates. MWI = microwave irradiation; LG ...