Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines

Sirotkina, Ekaterina V.; Efremova, Mariia M.; Старова, Галина Л.; Кузнецов, М. А.; Molchanov, A. P.

doi:10.1007/s10593-020-02797-z

Cited by 5 publications

(1 citation statement)

References 28 publications

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“…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 ]. The presence of additional functional groups in the isoxazolidine ring significantly expands the possibilities of using these substrates in organic synthesis [ 61 , 62 ].…”

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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