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The (3+2)- and formal (3+3)-cycloadditions of N-vinylpyrroles with cyclic nitrones and C,N-cyclic azomethine imines. / Афанасьева, Ксения Константиновна; Ефремова, Мария Михайловна; Кузнецова, Светлана; Иванов, Андрей Викторович; Старова, Галина Леонидовна; Молчанов, Александр Павлович.

в: Tetrahedron, Том 74, № 39, 27.09.2018, стр. 5665-5673.

Результаты исследований: Научные публикации в периодических изданияхстатьяРецензирование

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@article{12afadcc9695498da7cc2cfae0bad776,
title = "The (3+2)- and formal (3+3)-cycloadditions of N-vinylpyrroles with cyclic nitrones and C,N-cyclic azomethine imines",
abstract = "The addition of Lewis acids changes the path of the reaction of N-vinylpyrroles with 3,4-dihydroisoquinoline-N-oxides: formal (3 + 3)-cycloaddition proceeds instead of (3 + 2)-cycloaddition. In the case of benzoyl(3,4-dihydroisoquinolin-2-ium-2-yl)amides, reaction path does not change in the same conditions, but changing of the diastereoselectivity occurs and other diastereomer of (3 + 2)-cycloaddition became predominant.",
keywords = "Azomethine imines, Cycloaddition, GNJNIFCKGICBTH-NHCUHLMSSA-N, JNEUBRDFYRDDPT-ZJSXRUAMSA-N, JNLUFVKOOVHJHR-NFBKMPQASA-N, KUKRNRROWIPPLH-IEBWSBKVSA-N, Lewis acids, N-Vinylpyrroles, Nitrones, PSMOBIYCROTUKD-JWQCQUIFSA-N, PSMOBIYCROTUKD-LOSJGSFVSA-N, PUHBXAUATFXZEQ-CLJLJLNGSA-N, PUHBXAUATFXZEQ-IZZNHLLZSA-N, SFIAVDPJWKIVMG-RTBURBONSA-N, SHXDBJDCBZCNEY-DJJJIMSYSA-N, SHXDBJDCBZCNEY-ORAYPTAESA-N, SOMJEYSJUJWPEH-FGZHOGPDSA-N, UYMVUJUIBJFKTG-AOMKIAJQSA-N, UYMVUJUIBJFKTG-KSFYIVLOSA-N, VFFMOQKJYGWQDM-UHFFFAOYSA-N, WXKLUMIUZSABKP-FGZHOGPDSA-N, WYXDCYXJTVNCTP-YEJXKQKISA-N, WYXDCYXJTVNCTP-ZSEKCTLFSA-N, XWAFMJJPDVAYGS-WIYYLYMNSA-N, ZGCBHXQMMYLYBW-VSGBNLITSA-N, ZGCBHXQMMYLYBW-WUFINQPMSA-N",
author = "Афанасьева, {Ксения Константиновна} and Ефремова, {Мария Михайловна} and Светлана Кузнецова and Иванов, {Андрей Викторович} and Старова, {Галина Леонидовна} and Молчанов, {Александр Павлович}",
year = "2018",
month = sep,
day = "27",
doi = "10.1016/j.tet.2018.07.040",
language = "English",
volume = "74",
pages = "5665--5673",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",
number = "39",

}

RIS

TY - JOUR

T1 - The (3+2)- and formal (3+3)-cycloadditions of N-vinylpyrroles with cyclic nitrones and C,N-cyclic azomethine imines

AU - Афанасьева, Ксения Константиновна

AU - Ефремова, Мария Михайловна

AU - Кузнецова, Светлана

AU - Иванов, Андрей Викторович

AU - Старова, Галина Леонидовна

AU - Молчанов, Александр Павлович

PY - 2018/9/27

Y1 - 2018/9/27

N2 - The addition of Lewis acids changes the path of the reaction of N-vinylpyrroles with 3,4-dihydroisoquinoline-N-oxides: formal (3 + 3)-cycloaddition proceeds instead of (3 + 2)-cycloaddition. In the case of benzoyl(3,4-dihydroisoquinolin-2-ium-2-yl)amides, reaction path does not change in the same conditions, but changing of the diastereoselectivity occurs and other diastereomer of (3 + 2)-cycloaddition became predominant.

AB - The addition of Lewis acids changes the path of the reaction of N-vinylpyrroles with 3,4-dihydroisoquinoline-N-oxides: formal (3 + 3)-cycloaddition proceeds instead of (3 + 2)-cycloaddition. In the case of benzoyl(3,4-dihydroisoquinolin-2-ium-2-yl)amides, reaction path does not change in the same conditions, but changing of the diastereoselectivity occurs and other diastereomer of (3 + 2)-cycloaddition became predominant.

KW - Azomethine imines

KW - Cycloaddition

KW - GNJNIFCKGICBTH-NHCUHLMSSA-N

KW - JNEUBRDFYRDDPT-ZJSXRUAMSA-N

KW - JNLUFVKOOVHJHR-NFBKMPQASA-N

KW - KUKRNRROWIPPLH-IEBWSBKVSA-N

KW - Lewis acids

KW - N-Vinylpyrroles

KW - Nitrones

KW - PSMOBIYCROTUKD-JWQCQUIFSA-N

KW - PSMOBIYCROTUKD-LOSJGSFVSA-N

KW - PUHBXAUATFXZEQ-CLJLJLNGSA-N

KW - PUHBXAUATFXZEQ-IZZNHLLZSA-N

KW - SFIAVDPJWKIVMG-RTBURBONSA-N

KW - SHXDBJDCBZCNEY-DJJJIMSYSA-N

KW - SHXDBJDCBZCNEY-ORAYPTAESA-N

KW - SOMJEYSJUJWPEH-FGZHOGPDSA-N

KW - UYMVUJUIBJFKTG-AOMKIAJQSA-N

KW - UYMVUJUIBJFKTG-KSFYIVLOSA-N

KW - VFFMOQKJYGWQDM-UHFFFAOYSA-N

KW - WXKLUMIUZSABKP-FGZHOGPDSA-N

KW - WYXDCYXJTVNCTP-YEJXKQKISA-N

KW - WYXDCYXJTVNCTP-ZSEKCTLFSA-N

KW - XWAFMJJPDVAYGS-WIYYLYMNSA-N

KW - ZGCBHXQMMYLYBW-VSGBNLITSA-N

KW - ZGCBHXQMMYLYBW-WUFINQPMSA-N

UR - http://www.scopus.com/inward/record.url?scp=85051389575&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2018.07.040

DO - 10.1016/j.tet.2018.07.040

M3 - Article

VL - 74

SP - 5665

EP - 5673

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 39

ER -

ID: 35456850