Ambient access to a new family of pyrrole-fused pyrazine nitrones <i>via</i> 2-carbonyl-<i>N</i>-allenylpyrroles

Иванов, А. В.; Martynovskaya, Svetlana V.; Shcherbakova, V. S.; Ushakov, Igor А.; Bоrodinа, Tatyana N.; Bobkov, Alexander S.; Vitkovskaya, N. M.

doi:10.1039/d0qo00762e

Cited by 7 publications

(4 citation statements)

References 43 publications

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“…were detected, i.e., the reaction is highly chemo-and regioselective. Considering the fact that in the Schiff base only the E-isomer can easily form a 6-membered ring (it was previously shown 6 ), the reaction also features high stereoselectivity, since even no traces of a noncyclized Schiff base or 7-exo-dig cyclization product were detected. .…”

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confidence: 86%

“…Previously, we have employed an original building block, N -allenylpyrrole-2-carbaldehyde, as a key synthon for the construction of annulated pyrrole heterocycles to synthesize pyrrolopyrazine- N -oxides, benzimidazopyrrolopyrazines, and dihydrobenzimidazopyrrolopyrazines . The fundamental advantage of N -allenylpyrrole-2-carbaldehydes in cyclization reactions is that they allow the size of the closed ring to be easily controlled by varying the second reagent and substituents in the pyrrole counterpart.…”

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confidence: 99%

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Synthesis of Tetrazines from N-Allenylpyrrole-2-carbaldehydes and pH-Controlled Reversible Fragmentation

Martynovskaya,

Gyrgenova,

Ushakov

et al. 2023

Org. Lett.

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A one-pot highly selective approach to the synthesis of hitherto unknown tetrahydropyrrolo [2′,1′:3,4]pyrazino [1,2b]pyrrolo [2′,1′:3,4]pyrazino [1,2-e][1,2,4,5]tetrazine ensembles from simple and available N-allenylpyrrole-2-carbaldehydes and hydrazines has been developed. The reaction proceeds in a very facile manner and tolerates different substituents in both pyrroles and hydrazines. The novel class of organic compounds, tetrahydrodipyrrolodipyrazinotetrazines, proves to be promising pH-sensitive switchers to deliver N-aminopyrrolopyrazinium salts in acidic media and then again tetrahydrodipyrrolodipyrazinotetrazines in basic media. Both transformations give the products in quantitative yields.

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confidence: 86%

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confidence: 99%

Synthesis of Tetrazines from N-Allenylpyrrole-2-carbaldehydes and pH-Controlled Reversible Fragmentation

Martynovskaya,

Gyrgenova,

Ushakov

et al. 2023

Org. Lett.

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“…In the same year, Ivanov et al 46 described a metal-free cyclization of 2-carbonyl- N -allenylpyrroles 156 using hydroxyl amine. Oximes 157 were obtained through condensation of the hydroxyl amine on the carbonyl moiety and underwent a 6- exo-dig cyclization to form the pyrrole-fused pyrazines 158 .…”

Section: Hydrofunctionalizationsmentioning

confidence: 99%

Construction of C–N and C–O bonds based on N-allenamide functionalization

Hourtoule

Miesch

2022

Org. Biomol. Chem.

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“…The ability of nitrones to act as good radical traps has been widely researched over the last decades [1][2][3][4][5]. For years, nitrones have been used as efficient analytical tool for the detection and characterization of free radicals using EPR Spin Trapping Technique, based on their ability to quickly trap short-lived free radicals and afford persistent and identifiable aminoxyl spin adducts [6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of New Nitrone-Based Benzoxazinic Antioxidants

Marano

Minnelli

Mobbili

et al. 2020

The 1st International E-Conference on Antioxidants in Health and Disease

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Oxidative stress is often the cause of a wide range of human chronic pathologies including, but not limited to, stroke and cardiovascular and neurodegenerative diseases. In this setting, increasing efforts are currently being devoted to the design and synthesis of new derivatives with enhanced antioxidant efficacy. Among all the potential molecules of interest, synthetic nitrone spin-traps have attracted a great deal of research attention, particularly due to their dual function as effective inhibitors of oxidative stress and damage and as analytical tools for the detection and characterization of free radicals by means of the electron paramagnetic resonance (EPR) spectroscopy spin trapping technique. In this study, two derivatives of benzoxazinic nitrones (3-aryl-2H-benzo[1,4]oxazin-N-oxides) bearing an electron-withdrawing methyl-acetate group on the benzo moiety (in para and meta positions with respect to the nitronyl function) were synthesized. Their in vitro antioxidant activity was evaluated by means of the α,α-diphenyl-β-picrylhydrazyl radical (DPPH) scavenging assay, and their inhibitory effects on the erythrocyte hemolysis induced by the water-soluble free radical initiator 2,2′-azobis(2-amidinopropane) dihydrochloride (AAPH) compared. In addition, EPR was employed to monitor the decay profiles of DPPH to evaluate the kinetic behavior of the different antioxidants tested. Results showed that the presence and the position of the electron-withdrawing methyl-acetate group strongly affects the radical scavenging activity of nitrones. In particular, the newly synthesized para-substituted derivative, when compared to both the meta-substituted isomer and the unsubstituted parent compound, acts as a more effective antioxidant both in cell and cell-free systems. Overall, these results clearly show that the introduction of an electron-withdrawing group on the phenyl moiety significantly increased the antioxidant capacity of benzoxazinic nitrones, thus showing exciting opportunities in the search for new therapeutic agents in the treatment of diseases associated with oxidative stress.

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Ambient access to a new family of pyrrole-fused pyrazine nitrones via 2-carbonyl-N-allenylpyrroles

Abstract: The chemo-, regio- and stereoselective synthesis of pyrrole-fused pyrazine nitrones via the direct reaction of 2-carbonyl-N-allenylpyrroles (readily accessible from the corresponding NH-pyrroles) with hydroxyl amine hydrochloride has been developed. This...

Cited by 7 publications

References 43 publications

Synthesis of Tetrazines from N-Allenylpyrrole-2-carbaldehydes and pH-Controlled Reversible Fragmentation

Synthesis of Tetrazines from N-Allenylpyrrole-2-carbaldehydes and pH-Controlled Reversible Fragmentation

Construction of C–N and C–O bonds based on N-allenamide functionalization

Synthesis and Evaluation of New Nitrone-Based Benzoxazinic Antioxidants

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