Synthesis of 2-triazolylpurine Phosphonates

Kapilinskis, Zigfrīds; Novosjolova, Irina; Bizdēna, Ērika; Turks, Māris

doi:10.1007/s10593-021-02867-w

Cited by 3 publications

(2 citation statements)

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“…The major component was found to be partially reduced 2-triazolylpyrido [3,2-d]pyrimidine 7 (Scheme 6). We [36][37][38] and others [39] have previously observed that azido groups can be selectively reduced to their respective amino derivatives by Cu(I), which is generated by the CuSO4/ascorbate system.…”

Section: Synthesismentioning

confidence: 96%

SnAr Reactions of 2,4-Diazidopyrido[3,2-d]pyrimidine and Azide-Tetrazole Equilibrium Studies of the Obtained 5-Substituted Tetrazolo[1,5-a]pyrido[2,3-e]pyrimidines

et al. 2022

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A straightforward method for the synthesis of 5-substituted tetrazolo[1,5-a]pyrido[2,3-e]pyrimidines from 2,4-diazidopyrido[3,2-d]pyrimidine in SNAr reactions with N-, O-, and S- nucleophiles has been developed. The various N- and S-substituted products were obtained with yields from 47% to 98%, but the substitution with O-nucleophiles gave lower yields (20–32%). Furthermore, the fused tetrazolo[1,5-a]pyrimidine derivatives can be regarded as 2-azidopyrimidines and functionalized in copper(I)-catalyzed azide-alkyne dipolar cycloaddition (CuAAC) and Staudinger reactions due to the presence of a sufficient concentration of the reactive azide tautomer in solution. In total, seven products were fully characterized by their single crystal X-ray studies, while five of them were representatives of the tetrazolo[1,5-a]pyrido[2,3-e]pyrimidine heterocyclic system. Equilibrium constants and thermodynamic values were determined using variable temperature 1H NMR and are in agreement of favoring the tetrazole tautomeric form (ΔG298 = −3.33 to −7.52 (kJ/mol), ΔH = −19.92 to −48.02 (kJ/mol) and ΔS = −43.74 to −143.27 (J/mol·K)). The key starting material 2,4-diazidopyrido[3,2-d]pyrimidine presents a high degree of tautomerization in different solvents.

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Section: Synthesismentioning

confidence: 96%

SnAr Reactions of 2,4-Diazidopyrido[3,2-d]pyrimidine and Azide-Tetrazole Equilibrium Studies of the Obtained 5-Substituted Tetrazolo[1,5-a]pyrido[2,3-e]pyrimidines

et al. 2022

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“…Then, the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction provides the target product IV (Scheme 1, pathway A) [59][60][61]. Pathway B is designed on the basis of our group investigations on the synthesis of 2,6-bistriazolylpurine derivatives and their application in reactions with N-, S-and P-nucleophiles making use of regioselective S N Ar reactions at C(6) (V→VI→IV, Scheme 1) [11,14,62,63,77,78]. The main advantage of pathway B is a straightforward access to 2,6-diazidopurines V and 2,6-bistriazolylpurines VI due to excellent nucleophilic properties of the azide ion and wellestablished CuAAC reaction.…”

Section: Introductionmentioning

confidence: 99%

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

Cīrule¹,

Novosjolova²,

Bizdēna³

et al. 2021

Beilstein J. Org. Chem.

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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.

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Toward unsymmetrical 2,6-bistriazolylpurine nucleosides

Cīrule

Novosjolova

Spuris

et al. 2021

Chem Heterocycl Comp

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Synthesis of 2-triazolylpurine Phosphonates

Cited by 3 publications

References 14 publications

SnAr Reactions of 2,4-Diazidopyrido[3,2-d]pyrimidine and Azide-Tetrazole Equilibrium Studies of the Obtained 5-Substituted Tetrazolo[1,5-a]pyrido[2,3-e]pyrimidines

SnAr Reactions of 2,4-Diazidopyrido[3,2-d]pyrimidine and Azide-Tetrazole Equilibrium Studies of the Obtained 5-Substituted Tetrazolo[1,5-a]pyrido[2,3-e]pyrimidines

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

Toward unsymmetrical 2,6-bistriazolylpurine nucleosides

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Synthesis of 2-triazolylpurine Phosphonates

Cited by 3 publications

References 14 publications

SnAr Reactions of 2,4-Diazidopyrido[3,2-d]pyrimidine and Azide-Tetrazole Equilibrium Studies of the Obtained 5-Substituted Tetrazolo[1,5-a]pyrido[2,3-e]pyrimidines

SnAr Reactions of 2,4-Diazidopyrido[3,2-d]pyrimidine and Azide-Tetrazole Equilibrium Studies of the Obtained 5-Substituted Tetrazolo[1,5-a]pyrido[2,3-e]pyrimidines

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

Toward unsymmetrical 2,6-bistriazolylpurine nucleosides

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