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. 2021 Feb 11:17:410-419.
doi: 10.3762/bjoc.17.37. eCollection 2021.

1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles

Dace Cīrule  1 , Irina Novosjolova  1 , Ērika Bizdēna  1 , Māris Turks  1
Affiliations

1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles

Dace Cīrule et al. Beilstein J Org Chem. .

Abstract

A new approach was designed for the synthesis of C6-substituted 2-triazolylpurine derivatives. A series of substituted products was obtained in SNAr reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. The developed C-O and C-C bond forming reactions clearly show the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as leaving group.

Keywords: 2,6-bistriazolyl purines; nucleophilic aromatic substitution; purine nucleosides; triazoles.

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Figures

Scheme 1
Scheme 1
Synthetic pathways for the synthesis of 6-substituted 2-triazolylpurine derivatives IV.
Scheme 2
Scheme 2
Synthesis of 2,6-bistriazolylpurine derivatives 2a–c.
Scheme 3
Scheme 3
Synthesis of 6-alkyloxy-2-triazolylpurine derivatives 3a–f.
Scheme 4
Scheme 4
Synthesis of 6-alkyloxy-2-triazolylpurine nucleosides 3g–j.
Scheme 5
Scheme 5
2,6-Bistriazolylpurine derivatives in SNAr reactions with H2O/HO− as nucleophiles.
Scheme 6
Scheme 6
Synthesis of C6-substituted 2-triazolylpurine derivatives 5.
Figure 1
Figure 1
Possible tautomeric structures of compounds 5a–d.
See this image and copyright information in PMC

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