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