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

Research output

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.

Original languageEnglish
Pages (from-to)5665-5673
Number of pages9
JournalTetrahedron
Volume74
Issue number39
DOIs
Publication statusPublished - 27 Sep 2018

Fingerprint

Imines
Cycloaddition
Cycloaddition Reaction
Lewis Acids
Amides
Oxides
nitrones
azomethine
G 1616

Scopus subject areas

  • Chemistry(all)
  • Drug Discovery
  • Biochemistry
  • Organic Chemistry

Cite this

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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.",
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author = "Иванов, {Андрей Викторович} and Молчанов, {Александр Павлович} and Ефремова, {Мария Михайловна} and Старова, {Галина Леонидовна} and Афанасьева, {Ксения Константиновна} and Светлана Кузнецова",
year = "2018",
month = "9",
day = "27",
doi = "10.1016/j.tet.2018.07.040",
language = "English",
volume = "74",
pages = "5665--5673",
journal = "Tetrahedron",
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T1 - The (3+2)- and formal (3+3)-cycloadditions of N-vinylpyrroles with cyclic nitrones and C,N-cyclic azomethine imines

AU - Иванов, Андрей Викторович

AU - Молчанов, Александр Павлович

AU - Ефремова, Мария Михайловна

AU - Старова, Галина Леонидовна

AU - Афанасьева, Ксения Константиновна

AU - Кузнецова, Светлана

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.

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KW - Lewis acids

KW - N-Vinylpyrroles

KW - Nitrones

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KW - PSMOBIYCROTUKD-LOSJGSFVSA-N

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KW - SOMJEYSJUJWPEH-FGZHOGPDSA-N

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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 -