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Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines. / Sirotkina, Ekaterina V.; Efremova, Mariia M.; Starova, Galina L.; Kuznetsov, Mikhail A.; Molchanov, Alexander P.

In: Chemistry of Heterocyclic Compounds, Vol. 56, No. 9, 19.10.2020, p. 1193-1201.

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

Harvard

Sirotkina, EV, Efremova, MM, Starova, GL, Kuznetsov, MA & Molchanov, AP 2020, 'Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines', Chemistry of Heterocyclic Compounds, vol. 56, no. 9, pp. 1193-1201. https://doi.org/10.1007/s10593-020-02797-z

APA

Sirotkina, E. V., Efremova, M. M., Starova, G. L., Kuznetsov, M. A., & Molchanov, A. P. (2020). Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines. Chemistry of Heterocyclic Compounds, 56(9), 1193-1201. https://doi.org/10.1007/s10593-020-02797-z

Vancouver

Sirotkina EV, Efremova MM, Starova GL, Kuznetsov MA, Molchanov AP. Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines. Chemistry of Heterocyclic Compounds. 2020 Oct 19;56(9):1193-1201. https://doi.org/10.1007/s10593-020-02797-z

Author

Sirotkina, Ekaterina V. ; Efremova, Mariia M. ; Starova, Galina L. ; Kuznetsov, Mikhail A. ; Molchanov, Alexander P. / Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines. In: Chemistry of Heterocyclic Compounds. 2020 ; Vol. 56, No. 9. pp. 1193-1201.

BibTeX

@article{b631ae54a8254c939880ee0a9a67c5d1,
title = "Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines",
abstract = "Ketonitrones containing two ester groups react regio- and stereoselectively with 1,3-diarylpropenones to form isoxazolidines with ester groups at position 3 of the ring. The action of zinc in acetic acid on these isoxazolidines causes opening of the ring with the formation of 3-amino alcohols, the subsequent cyclization of which leads to polysubstituted lactones. Reduction of the benzoyl group of isoxazolidine with sodium borohydride leads, as a result of subsequent transformations, to the formation of substituted 1,3,4-triaryl-6-oxodihydro-1H,3H-furo[3,4-c]isoxazole-6a(6H)-carboxylates as single diastereomers.",
keywords = "изоксазолидины, нитроны, халконы, 1,3-диполярное циклоприсоединение, восстановление., 1,3-dipolar cycloaddition, chalcones, isoxazolidines, nitrones, reduction, INHIBITION, DIASTEREOSELECTIVITY, 1,3-DIPOLAR CYCLOADDITION, BIOLOGICAL EVALUATION, STEREOSELECTIVE CYCLOADDITION",
author = "Sirotkina, {Ekaterina V.} and Efremova, {Mariia M.} and Starova, {Galina L.} and Kuznetsov, {Mikhail A.} and Molchanov, {Alexander P.}",
note = "Статья в журнале",
year = "2020",
month = oct,
day = "19",
doi = "10.1007/s10593-020-02797-z",
language = "English",
volume = "56",
pages = "1193--1201",
journal = "Chemistry of Heterocyclic Compounds",
issn = "0009-3122",
publisher = "Springer Nature",
number = "9",

}

RIS

TY - JOUR

T1 - Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines

AU - Sirotkina, Ekaterina V.

AU - Efremova, Mariia M.

AU - Starova, Galina L.

AU - Kuznetsov, Mikhail A.

AU - Molchanov, Alexander P.

N1 - Статья в журнале

PY - 2020/10/19

Y1 - 2020/10/19

N2 - Ketonitrones containing two ester groups react regio- and stereoselectively with 1,3-diarylpropenones to form isoxazolidines with ester groups at position 3 of the ring. The action of zinc in acetic acid on these isoxazolidines causes opening of the ring with the formation of 3-amino alcohols, the subsequent cyclization of which leads to polysubstituted lactones. Reduction of the benzoyl group of isoxazolidine with sodium borohydride leads, as a result of subsequent transformations, to the formation of substituted 1,3,4-triaryl-6-oxodihydro-1H,3H-furo[3,4-c]isoxazole-6a(6H)-carboxylates as single diastereomers.

AB - Ketonitrones containing two ester groups react regio- and stereoselectively with 1,3-diarylpropenones to form isoxazolidines with ester groups at position 3 of the ring. The action of zinc in acetic acid on these isoxazolidines causes opening of the ring with the formation of 3-amino alcohols, the subsequent cyclization of which leads to polysubstituted lactones. Reduction of the benzoyl group of isoxazolidine with sodium borohydride leads, as a result of subsequent transformations, to the formation of substituted 1,3,4-triaryl-6-oxodihydro-1H,3H-furo[3,4-c]isoxazole-6a(6H)-carboxylates as single diastereomers.

KW - изоксазолидины, нитроны, халконы, 1,3-диполярное циклоприсоединение, восстановление.

KW - 1,3-dipolar cycloaddition

KW - chalcones

KW - isoxazolidines

KW - nitrones

KW - reduction

KW - INHIBITION

KW - DIASTEREOSELECTIVITY

KW - 1,3-DIPOLAR CYCLOADDITION

KW - BIOLOGICAL EVALUATION

KW - STEREOSELECTIVE CYCLOADDITION

UR - http://www.scopus.com/inward/record.url?scp=85092691495&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/75ea04ec-2966-3ebf-9833-9cf0f982d4c4/

U2 - 10.1007/s10593-020-02797-z

DO - 10.1007/s10593-020-02797-z

M3 - Article

AN - SCOPUS:85092691495

VL - 56

SP - 1193

EP - 1201

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 9

ER -

ID: 70435144