The 1,3-dipolar cycloaddition of adamantine-derived nitrones with maleimides

Molchanov, A. P.; Lukina, Valentina M.; Efremova, Mariia M.; Мурылева, Анна А.; Slita, Alexander V.; Zarubaev, Vladimir V.

doi:10.1080/00397911.2020.1738494

Cited by 8 publications

(6 citation statements)

References 44 publications

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“…Reversibility was observed for the 1,3-dipolar cycloaddition reactions of nitrones [ 50 , 63 ]. In our case, the ratio of isomeric compounds 3 and 3′ depends on the reaction temperature.…”

Section: Resultsmentioning

confidence: 99%

“…Isoxazolidine derivatives, the products of the cycloaddition of nitrones to the C=C bond, are of considerable interest due to the wide range of their biological properties [ 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 ]. Moreover, due to the ease of the N–O bond cleavage in the isoxazolidine ring under reductive conditions, these compounds can be used for the synthesis of 1,3-aminoalcohols [ 52 , 53 , 54 ], biologically valuable β-lactams [ 55 , 56 , 57 , 58 , 59 ], and amino acids [ 60 ].…”

Section: Introductionmentioning

confidence: 99%

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Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines

Kartsev

Efremova

Molchanov

et al. 2022

IJMS

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The 1,3-dipolar cycloaddition of 2-(2-oxoindoline-3-ylidene)acetates with functionalized aldo- and ketonitrones proceeds with good selectivity to provide new highly functionalized 5-spiroisoxazolidines. A characteristic feature of these reactions is reversibility that allows for the control of the diastereoselectivity of cycloaddition. The reduction of obtained adducts using zinc powder in acetic acid leads to 1,3-aminoalcohols or spirolactones. For a number of the spiro compounds obtained, anticancer activity was found.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines

Kartsev

Efremova

Molchanov

et al. 2022

IJMS

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“…In 2020, the 1,3-DC of adamantine aldo and ketonitrones with maleimides leading to isoxazolidines appeared in the literature [69]. From an experimental point of view, the reaction was conducted in toluene at 110 • C. In the case of 185, a diastereomeric mixture was obtained, while in the case of 181, only one isomer is achieved (Scheme 48).…”

Section: Nitronesmentioning

confidence: 99%

Section: Nitronesmentioning

confidence: 99%

Density Functional Theory Calculations: A Useful Tool to Investigate Mechanisms of 1,3-Dipolar Cycloaddition Reactions

Chiacchio,

Legnani

2024

IJMS

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The present review contains a representative sampling of mechanistic studies, which have appeared in the literature in the last 5 years, on 1,3-dipolar cycloaddition reactions, using DFT calculations. Attention is focused on the mechanistic insights into 1,3-dipoles of propargyl/allenyl type and allyl type such as aza-ylides, nitrile oxides and azomethyne ylides and nitrones, respectively. The important role played by various metal–chiral–ligand complexes and the use of chiral eductors in promoting the site-, regio-, diastereo- and enatioselectivity of the reaction are also outlined.

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“…The cytotoxic and virus-inhibiting activity against influenza virus was investigated for selected adducts with moderate toxicity but low antiviral activities. 42 Scheme 12. Synthetic general pathways to maleinide-isoxazolidine derivatives.…”

Section: Scheme 7 Synthesis Of (3-diethoxyphosphoryl)-isoxazolidines ...mentioning

confidence: 99%

Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions. Part 2: nitrones, nitrile oxides and imines, and other 1,3-dipoles

Quadrelli¹,

Mella²,

Faita³

2023

Arkivoc

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Prominent in the current stage of drug development, antiviral compounds can be efficiently prepared through cycloaddition reactions. This review reports the use of 1,3-dipolar cycloadditions of nitrones, nitrile oxides and imines and other 1,3-dipoles in the light of their application for the preparation of synthons in the design and synthesis of compounds that were tested for their antiviral activities against a variety of viruses. Since nitrile oxides represent valuable precursors of nitrosocarbonyl intermediates, their use in the synthesis of antiviral compounds is reported. The products obtained from these pericyclic reaction approaches were tested for their activities in terms of blocking the virus replication and the relevant biological data are highlighted.

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The 1,3-dipolar cycloaddition of adamantine-derived nitrones with maleimides

Cited by 8 publications

References 44 publications

Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines

Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines

Density Functional Theory Calculations: A Useful Tool to Investigate Mechanisms of 1,3-Dipolar Cycloaddition Reactions

Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions. Part 2: nitrones, nitrile oxides and imines, and other 1,3-dipoles

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