Synthesis and study of the azide-tetrazole tautomerism in 2-azido-4-(trifluoromethyl)-6-R-pyrimidines (R = H, 4-ClC6H4)

Николаенкова, Елена Б.; Aleksandrova, N. V.; Mamatyuk, V. I.; Krivopalov, V. P.

doi:10.1007/s11172-018-2154-z

Cited by 9 publications

(1 citation statement)

References 33 publications

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“…A significant shift in the equilibrium between the cyclic tetrazole and open-chain azide forms may affect the activity of the compound in chemical reactions, making it important to establish the state of the reacting compounds. The chemical shifts in the natural-abundance 1D 1 H and 13 C NMR spectra are usually used to determine the state of azide–tetrazole equilibrium in solution . However, the application of 15 N NMR spectroscopy is very promising for studying the nitrogen-rich compounds .…”

Section: Introductionmentioning

confidence: 99%

¹⁵N Chemical Shifts and J_NN-Couplings as Diagnostic Tools for Determination of the Azide–Tetrazole Equilibrium in Tetrazoloazines

et al. 2021

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Selectively 15N-labeled tetrazolo[1,5-b][1,2,4]triazines and tetrazolo[1,5-a]pyrimidines bearing one, two, or three 15N labels were synthesized. The synthesized compounds were studied by 1H, 13C, and 15N NMR spectroscopy in DMSO and TFA solutions, where the azide–tetrazole equilibrium can lead to the formation of two tetrazole (T, T′) isomers and one azide (A) isomer for each compound. Incorporation of the 15N-label(s) leads to the appearance of 15N–15N coupling constants (J NN), which can be easily measured via simple 1D 15N NMR spectra, even at natural abundance between labeled and unlabeled 15N atoms. The chemical shifts for the 15N nuclei in the azole moiety are very sensitive to the ring opening and azide formation, thus providing information about the azido–tetrazole equilibrium. At the same time, the 1–2 J NN couplings between 15N-labeled atoms in the azole and azine fragments unambiguously determine the fusion type between tetrazole and azine rings in the cyclic isomers T and T′. Thus, combined analysis of 15N chemical shifts and J NN values in selectively isotope-enriched compounds provides an effective diagnostic tool for direct structural determination of tetrazole isomers and azide form in solution. This method was found to be the most simple and efficient way to study the azido–tetrazole equilibrium.

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Section: Introductionmentioning

confidence: 99%

¹⁵N Chemical Shifts and J_NN-Couplings as Diagnostic Tools for Determination of the Azide–Tetrazole Equilibrium in Tetrazoloazines

et al. 2021

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Recent investigations and applications of azidoazomethine-tetrazole tautomeric equilibrium (microreview)

Sebris

Turks

2019

Chem Heterocycl Comp

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Synthesis and study of azide-tetrazole tautomerism in 2-azido-6-phenylpyrimidin-4(3H)-one and 2-azido-4-chloro-6-phenylpyrimidine

et al. 2022

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Synthesis and study of the azide-tetrazole tautomerism in 2-azido-4-(trifluoromethyl)-6-R-pyrimidines (R = H, 4-ClC6H4)

Cited by 9 publications

References 33 publications

¹⁵N Chemical Shifts and J_NN-Couplings as Diagnostic Tools for Determination of the Azide–Tetrazole Equilibrium in Tetrazoloazines

¹⁵N Chemical Shifts and J_NN-Couplings as Diagnostic Tools for Determination of the Azide–Tetrazole Equilibrium in Tetrazoloazines

Recent investigations and applications of azidoazomethine-tetrazole tautomeric equilibrium (microreview)

Synthesis and study of azide-tetrazole tautomerism in 2-azido-6-phenylpyrimidin-4(3H)-one and 2-azido-4-chloro-6-phenylpyrimidine

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Synthesis and study of the azide-tetrazole tautomerism in 2-azido-4-(trifluoromethyl)-6-R-pyrimidines (R = H, 4-ClC6H4)

Cited by 9 publications

References 33 publications

15N Chemical Shifts and JNN-Couplings as Diagnostic Tools for Determination of the Azide–Tetrazole Equilibrium in Tetrazoloazines

15N Chemical Shifts and JNN-Couplings as Diagnostic Tools for Determination of the Azide–Tetrazole Equilibrium in Tetrazoloazines

Recent investigations and applications of azidoazomethine-tetrazole tautomeric equilibrium (microreview)

Synthesis and study of azide-tetrazole tautomerism in 2-azido-6-phenylpyrimidin-4(3H)-one and 2-azido-4-chloro-6-phenylpyrimidine

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¹⁵N Chemical Shifts and J_NN-Couplings as Diagnostic Tools for Determination of the Azide–Tetrazole Equilibrium in Tetrazoloazines

¹⁵N Chemical Shifts and J_NN-Couplings as Diagnostic Tools for Determination of the Azide–Tetrazole Equilibrium in Tetrazoloazines