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Highly efficient and stereoselective cycloaddition of nitrones to indolyl- and pyrrolylacrylates. / Dmitriev, Viktor A.; Efremova, Mariia M.; Novikov, Alexander S.; Zarubaev, Vladimir V.; Slita, Alexander V.; Galochkina, Anastasia V.; Starova, Galina L.; Ivanov, Andrey V.; Molchanov, Alexander P.

In: Tetrahedron Letters, Vol. 59, No. 24, 13.06.2018, p. 2327 - 2331.

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Author

Dmitriev, Viktor A. ; Efremova, Mariia M. ; Novikov, Alexander S. ; Zarubaev, Vladimir V. ; Slita, Alexander V. ; Galochkina, Anastasia V. ; Starova, Galina L. ; Ivanov, Andrey V. ; Molchanov, Alexander P. / Highly efficient and stereoselective cycloaddition of nitrones to indolyl- and pyrrolylacrylates. In: Tetrahedron Letters. 2018 ; Vol. 59, No. 24. pp. 2327 - 2331.

BibTeX

@article{a40320ea7798452c8915dcb30beb3173,
title = "Highly efficient and stereoselective cycloaddition of nitrones to indolyl- and pyrrolylacrylates",
abstract = "The reactions of various nitrones with indolyl- and pyrrolylacrylates proceeds regioselectively with high diastereoselectivity in the case of aldonitrones, and represents an effective method for obtaining new indolyl- and pyrrolyl-substituted isoxazolidine carboxylates stabilized by weak (C–H⋯O) and moderate (N–H⋯N) strength intramolecular hydrogen bonding. The resulting cycloadducts exhibit promising in vitro anti-influenza activities.",
keywords = "Cycloaddition, Indoles, Isoxazolidines, Nitrones, HYDROGEN-BOND, EASY ACCESS, N-VINYLPYRROLES, PYRROLES, SOLID-STATE, AZOMETHINE IMINES, MEDICINAL CHEMISTRY, ISOXAZOLIDINES, NITRILE OXIDES, 1,3-DIPOLAR CYCLOADDITION",
author = "Dmitriev, {Viktor A.} and Efremova, {Mariia M.} and Novikov, {Alexander S.} and Zarubaev, {Vladimir V.} and Slita, {Alexander V.} and Galochkina, {Anastasia V.} and Starova, {Galina L.} and Ivanov, {Andrey V.} and Molchanov, {Alexander P.}",
note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",
year = "2018",
month = jun,
day = "13",
doi = "10.1016/j.tetlet.2018.04.066",
language = "English",
volume = "59",
pages = "2327 -- 2331",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",
number = "24",

}

RIS

TY - JOUR

T1 - Highly efficient and stereoselective cycloaddition of nitrones to indolyl- and pyrrolylacrylates

AU - Dmitriev, Viktor A.

AU - Efremova, Mariia M.

AU - Novikov, Alexander S.

AU - Zarubaev, Vladimir V.

AU - Slita, Alexander V.

AU - Galochkina, Anastasia V.

AU - Starova, Galina L.

AU - Ivanov, Andrey V.

AU - Molchanov, Alexander P.

N1 - Publisher Copyright: © 2018 Elsevier Ltd

PY - 2018/6/13

Y1 - 2018/6/13

N2 - The reactions of various nitrones with indolyl- and pyrrolylacrylates proceeds regioselectively with high diastereoselectivity in the case of aldonitrones, and represents an effective method for obtaining new indolyl- and pyrrolyl-substituted isoxazolidine carboxylates stabilized by weak (C–H⋯O) and moderate (N–H⋯N) strength intramolecular hydrogen bonding. The resulting cycloadducts exhibit promising in vitro anti-influenza activities.

AB - The reactions of various nitrones with indolyl- and pyrrolylacrylates proceeds regioselectively with high diastereoselectivity in the case of aldonitrones, and represents an effective method for obtaining new indolyl- and pyrrolyl-substituted isoxazolidine carboxylates stabilized by weak (C–H⋯O) and moderate (N–H⋯N) strength intramolecular hydrogen bonding. The resulting cycloadducts exhibit promising in vitro anti-influenza activities.

KW - Cycloaddition

KW - Indoles

KW - Isoxazolidines

KW - Nitrones

KW - HYDROGEN-BOND

KW - EASY ACCESS

KW - N-VINYLPYRROLES

KW - PYRROLES

KW - SOLID-STATE

KW - AZOMETHINE IMINES

KW - MEDICINAL CHEMISTRY

KW - ISOXAZOLIDINES

KW - NITRILE OXIDES

KW - 1,3-DIPOLAR CYCLOADDITION

UR - http://www.scopus.com/inward/record.url?scp=85047061589&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/highly-efficient-stereoselective-cycloaddition-nitrones-indolyl-pyrrolylacrylates

U2 - 10.1016/j.tetlet.2018.04.066

DO - 10.1016/j.tetlet.2018.04.066

M3 - Article

VL - 59

SP - 2327

EP - 2331

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 24

ER -

ID: 33236526