Heterocyclic compounds of marine organisms (review)

Elyakov, G. B.; Stonik, Valentin A.; Makar’eva, T. N.

doi:10.1007/bf00482772

Cited by 4 publications

(1 citation statement)

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“…Derivatives of 1,2,4-triazines and pyrimidines present an important core in many natural − and synthetic − biologically active compounds. These heterocycles easily undergo different substitution reactions and ring transformations − that make them convenient precursors for the synthesis of other heteroaromatic compounds, e.g., azoloazines. , The transformations of the azine ring by the Dimrorth rearrangement can easily change the type of fusion between the azole and azine rings. − Therefore, the unambiguous determination of the fusion type in azoloazines becomes an important task in organic chemistry. − A similar problem arises from the possibility of a structural rearrangement in the azole ring.…”

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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Experimental and DFT studies on the vibrational and electronic spectra of 4,5-dihydro-6-methyl-4-[(E)-(3-pyridinylmethylene)amino]-1,2,4-triazin-3(2H)-one

Zhang¹,

Zhou²,

Jiang³

et al. 2011

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Marine paralytic shellfish toxins: chemical properties, mode of action, newer analogues, and structure–toxicity relationship

Leal

Cristiano

2022

Nat. Prod. Rep.

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Heterocyclic compounds of marine organisms (review)

Cited by 4 publications

References 121 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

Experimental and DFT studies on the vibrational and electronic spectra of 4,5-dihydro-6-methyl-4-[(E)-(3-pyridinylmethylene)amino]-1,2,4-triazin-3(2H)-one

Marine paralytic shellfish toxins: chemical properties, mode of action, newer analogues, and structure–toxicity relationship

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Heterocyclic compounds of marine organisms (review)

Cited by 4 publications

References 121 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

Experimental and DFT studies on the vibrational and electronic spectra of 4,5-dihydro-6-methyl-4-[(E)-(3-pyridinylmethylene)amino]-1,2,4-triazin-3(2H)-one

Marine paralytic shellfish toxins: chemical properties, mode of action, newer analogues, and structure–toxicity relationship

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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