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

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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. / Karcev, Dmitriy D. ; Efremova, Mariia M. ; Molchanov, Alexander P. ; Rostovskii, Nikolai V. ; Kryukova, Mariya A.; Bunev, Alexander S. ; Khochenkov, Dmitry A. .

In: International Journal of Molecular Sciences, Vol. 23, No. 20, 12639, 20.10.2022.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{5d35f44dc8914ac687f8843d02a7cf07,

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

abstract = "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 compoundsobtained, anticancer activity was found.",

keywords = "1,3-dipolar cycloaddition, spiroisoxazolidines, nitrones, regioselectivity, diastereoselectivity",

author = "Karcev, {Dmitriy D.} and Efremova, {Mariia M.} and Molchanov, {Alexander P.} and Rostovskii, {Nikolai V.} and Kryukova, {Mariya A.} and Bunev, {Alexander S.} and Khochenkov, {Dmitry A.}",

note = "Publisher Copyright: {\textcopyright} 2022 by the authors.",

year = "2022",

month = oct,

day = "20",

doi = "10.3390/ijms232012639",

language = "English",

volume = "23",

journal = "International Journal of Molecular Sciences",

issn = "1422-0067",

publisher = "MDPI AG",

number = "20",

}

RIS

TY - JOUR

T1 - Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines

AU - Karcev, Dmitriy D.

AU - Efremova, Mariia M.

AU - Molchanov, Alexander P.

AU - Rostovskii, Nikolai V.

AU - Kryukova, Mariya A.

AU - Bunev, Alexander S.

AU - Khochenkov, Dmitry A.

PY - 2022/10/20

Y1 - 2022/10/20

N2 - 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 compoundsobtained, anticancer activity was found.

AB - 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 compoundsobtained, anticancer activity was found.

KW - 1,3-dipolar cycloaddition

KW - spiroisoxazolidines

KW - nitrones

KW - regioselectivity

KW - diastereoselectivity

UR - http://www.scopus.com/inward/record.url?scp=85140811710&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/68267d75-acff-3176-97a5-e9234b6e09d6/

U2 - 10.3390/ijms232012639

DO - 10.3390/ijms232012639

M3 - Article

VL - 23

JO - International Journal of Molecular Sciences

JF - International Journal of Molecular Sciences

SN - 1422-0067

IS - 20

M1 - 12639

ER -

ID: 99997130