Reactions of azinium cations. 8. Electron structures of 3-substituted 1,2,4-triazines and protonation, quaternization, and reactions with nucleophiles

Алексеев, С. Г.; Torgashev, P. A.; Fedotov, M. A.; Rezvukhin, A. I.; Shorshnev, S. V.; Belik, A. V.; Charushin, Valery N.; Чупахин, О. Н.

doi:10.1007/bf00478865

Cited by 3 publications

(1 citation statement)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It should also be noted that in doubly 1 H, 15 N-decoupled 1D 13 C NMR spectrum of a 12*a,bT and 12*a,bA mixture the C11/C15 resonances of phenyl substitutes of both the tetrazole and azide forms demonstrated additional splitting (data not shown). These effects can be ascribed to the possible protonation of different nitrogen atoms of the 1,2,4-triazine fragment under acidic conditions …”

Section: Resultsmentioning

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

View full text Add to dashboard Cite

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.

show abstract

Section: Resultsmentioning

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

View full text Add to dashboard Cite

show abstract

Synthesis and transformations of 4-phenylethynyl- and 4-styrylpyrazolo[5,1-c][1,2,4]triazines

Иванов

Koltun

2021

Chem Heterocycl Comp

View full text Add to dashboard Cite

1,4-Oxazines and their Benzo Derivatives

Aitken

2008

Comprehensive Heterocyclic Chemistry III

View full text Add to dashboard Cite

Reactions of azinium cations. 8. Electron structures of 3-substituted 1,2,4-triazines and protonation, quaternization, and reactions with nucleophiles

Cited by 3 publications

References 23 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

Synthesis and transformations of 4-phenylethynyl- and 4-styrylpyrazolo[5,1-c][1,2,4]triazines

1,4-Oxazines and their Benzo Derivatives

Contact Info

Product

Resources

About

Reactions of azinium cations. 8. Electron structures of 3-substituted 1,2,4-triazines and protonation, quaternization, and reactions with nucleophiles

Cited by 3 publications

References 23 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

Synthesis and transformations of 4-phenylethynyl- and 4-styrylpyrazolo[5,1-c][1,2,4]triazines

1,4-Oxazines and their Benzo Derivatives

Contact Info

Product

Resources

About

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