Ethyl cyanoacetate as 1,3-bifunctional reagent in the pyrimidine to pyridine ring transformations

Чупахин, О. Н.; Русинов, В. Л.; Tumashov, A. A.; Sidorov, E. O.; Karpin, I. V.

doi:10.1016/s0040-4039(00)92539-5

Cited by 14 publications

(3 citation statements)

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“…15 N-isotopic labeling of heterocyclic compounds increases significantly the breadth of NMR methods that can be used for determination of molecular structures and mechanisms of chemical rearrangements in solution. [35][36][37] In the case of tetrazoloazines, the chemical shifts of the labeled 15 N atoms can be an indicator for either the azide or tetrazole forms of the molecule. [38][39][40][41][42][43][44] Heteronuclear 1 H- 15 N and 13 C- 15 N J couplings (J HN and J CN ) give direct information about chemical structure.…”

Section: Introductionmentioning

confidence: 99%

Selective ¹⁵N-Labeling and Analysis of ¹³C−¹⁵N J Couplings as an Effective Tool for Studying the Structure and Azide−Tetrazole Equilibrium in a Series of Tetrazolo[1,5-b][1,2,4]triazines and Tetrazolo[1,5-a]pyrimidines

et al. 2010

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Two general methods for the selective incorporation of an (15)N-label in the azole ring of tetrazolo[1,5-b][1,2,4]triazines and tetrazolo[1,5-a]pyrimidines were developed. The first approach included treatment of azinylhydrazides with (15)N-labeled nitrous acid, and the second approach was based on fusion of the azine ring to [2-(15)N]-5-aminotetrazole. The synthesized compounds were studied by (1)H, (13)C, and (15)N NMR spectroscopy in both DMSO and TFA solution, in which the azide-tetrazole equilibrium is shifted to tetrazole and azide forms, respectively. Incorporation of the (15)N-label led to the appearance of (13)C-(15)N J coupling constants (J(CN)), which can be measured easily using either 1D (13)C spectra with selective (15)N decoupling or with amplitude modulated 1D (13)C spin-echo experiments with selective inversion of the (15)N nuclei. The observed J(CN) patterns permit unambiguous determination of the type of fusion between the azole and azine rings in tetrazolo[1,5-b][1,2,4]triazine derivatives. Joint analysis of J(CN) patterns and (15)N chemical shifts was found to be the most efficient way to study the azido-tetrazole equilibrium.

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Section: Introductionmentioning

confidence: 99%

Selective ¹⁵N-Labeling and Analysis of ¹³C−¹⁵N J Couplings as an Effective Tool for Studying the Structure and Azide−Tetrazole Equilibrium in a Series of Tetrazolo[1,5-b][1,2,4]triazines and Tetrazolo[1,5-a]pyrimidines

et al. 2010

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“…The study of the interaction between dinitrofurazone 50* and indene using a 15 45,46 It was found that 13…”

Section: Scheme 18mentioning

confidence: 99%

“…The application of double-labeled 13 C, 15 N-ethyl cyanoacetate 38* permitted the detection of the Dimroth rearrangement for nitro-1,2,4-triazolo[1,5- a ]pyrimidine 71 ( Scheme 25 ). 45,46 …”

Section: Analysis Of J Cn and ...mentioning

confidence: 99%

¹⁵N labeling and analysis of¹³C–¹⁵N and¹H–¹⁵N couplings in studies of the structures and chemical transformations of nitrogen heterocycles

et al. 2019

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Nitroazines 25. Spectral study of the reaction of the transformation of 6-Nitroazolo[1,5-a]Pyrimidines by CH-active nitriles

Русинов¹,

Pilicheva²,

Tumashov³

et al. 1994

Chem Heterocycl Compd

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Ethyl cyanoacetate as 1,3-bifunctional reagent in the pyrimidine to pyridine ring transformations

Cited by 14 publications

References 5 publications

Selective ¹⁵N-Labeling and Analysis of ¹³C−¹⁵N J Couplings as an Effective Tool for Studying the Structure and Azide−Tetrazole Equilibrium in a Series of Tetrazolo[1,5-b][1,2,4]triazines and Tetrazolo[1,5-a]pyrimidines

Selective ¹⁵N-Labeling and Analysis of ¹³C−¹⁵N J Couplings as an Effective Tool for Studying the Structure and Azide−Tetrazole Equilibrium in a Series of Tetrazolo[1,5-b][1,2,4]triazines and Tetrazolo[1,5-a]pyrimidines

¹⁵N labeling and analysis of¹³C–¹⁵N and¹H–¹⁵N couplings in studies of the structures and chemical transformations of nitrogen heterocycles

Nitroazines 25. Spectral study of the reaction of the transformation of 6-Nitroazolo[1,5-a]Pyrimidines by CH-active nitriles

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Ethyl cyanoacetate as 1,3-bifunctional reagent in the pyrimidine to pyridine ring transformations

Cited by 14 publications

References 5 publications

Selective 15N-Labeling and Analysis of 13C−15N J Couplings as an Effective Tool for Studying the Structure and Azide−Tetrazole Equilibrium in a Series of Tetrazolo[1,5-b][1,2,4]triazines and Tetrazolo[1,5-a]pyrimidines

Selective 15N-Labeling and Analysis of 13C−15N J Couplings as an Effective Tool for Studying the Structure and Azide−Tetrazole Equilibrium in a Series of Tetrazolo[1,5-b][1,2,4]triazines and Tetrazolo[1,5-a]pyrimidines

15N labeling and analysis of13C–15N and1H–15N couplings in studies of the structures and chemical transformations of nitrogen heterocycles

Nitroazines 25. Spectral study of the reaction of the transformation of 6-Nitroazolo[1,5-a]Pyrimidines by CH-active nitriles

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Selective ¹⁵N-Labeling and Analysis of ¹³C−¹⁵N J Couplings as an Effective Tool for Studying the Structure and Azide−Tetrazole Equilibrium in a Series of Tetrazolo[1,5-b][1,2,4]triazines and Tetrazolo[1,5-a]pyrimidines

Selective ¹⁵N-Labeling and Analysis of ¹³C−¹⁵N J Couplings as an Effective Tool for Studying the Structure and Azide−Tetrazole Equilibrium in a Series of Tetrazolo[1,5-b][1,2,4]triazines and Tetrazolo[1,5-a]pyrimidines

¹⁵N labeling and analysis of¹³C–¹⁵N and¹H–¹⁵N couplings in studies of the structures and chemical transformations of nitrogen heterocycles