Regioselective cycloaddition of C,N-diarylnitrones to arylallenes and of N-aryl-C-carbamoylnitrones to methyl buta-2,3-dienoate

Molchanov, A. P.; Malinina, Yu.; Kostikov, R. R.; Stepakov, A. V.

doi:10.1134/s1070428015030136

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Cited by 4 publications

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“…Previously, the reactions with aldonitrones that did not contain additional functional groups were most studied. However, it is known that the transition from aldo- to ketonitrones or the introduction of additional functional groups in the α-position of the nitrone can dramatically affect the regio- and stereoselectivity of the 1,3-dipolar cycloaddition reactions [ 38 , 39 , 40 ].…”

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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Section: Introductionmentioning

confidence: 99%