Regio- and diastereoselectivity of the cycloaddition of aldonitrones with benzylidenecyclopropane: An experimental and theoretical study

Sirotkina, Ekaterina V.; Efremova, Mariia M.; Novikov, Alexander S.; Zarubaev, Vladimir V.; Orshanskaya, Iana R.; Старова, Галина Л.; Kostikov, R. R.; Molchanov, A. P.

doi:10.1016/j.tet.2017.04.014

Cited by 26 publications

(2 citation statements)

References 34 publications

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“…This increase in anti-viral activity was due to increased affinity to the target, as the values of toxicity did not change significantly. 40 Cycloaddition reactions of N-allyl substituted polycyclic derivatives of isoindole-1,3-dione with nitrones were investigated and the authors demonstrate the reactions proceed regio-and stereoselectively on the C=C double bond of the N-allyl substituent affording the substituted isoxazolidines in good yields (Scheme 11). Scheme 11.…”

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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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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“…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%

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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Synthesis of N‐Aryl Isoxazolidines by Photo‐Promoted N‐Selective Arylation of Oximes and Cyclization Using Hypervalent Iodine Reagents and Copper Catalyst

et al. 2023

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Oximes cause photo‐promoted, copper‐catalyzed N‐selective arylation with diaryl iodonium salts to produce nitrones, which in turn undergo intra‐ or intermolecular 1,3‐dipolar cyclization with olefins to afford N‐aryl isoxazolidines. Hypervalent iodine reagents substituted with either electron‐rich or electron‐deficient groups afford the corresponding N‐aryl isoxazolidines in 26–95% yields. This method offers a faster reaction rate, lower catalyst loading and broader substrate scope of oxime than similar nitrone syntheses employing Chan‐Lam‐Evans coupling. The reaction involves via a radical/single electron transfer (SET) pathway, and does not proceed in the absence of photoirradiation.

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Regio- and diastereoselectivity of the cycloaddition of aldonitrones with benzylidenecyclopropane: An experimental and theoretical study

Cited by 26 publications

References 34 publications

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

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

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

Synthesis of N‐Aryl Isoxazolidines by Photo‐Promoted N‐Selective Arylation of Oximes and Cyclization Using Hypervalent Iodine Reagents and Copper Catalyst

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