Standard

Highly Efficient Synthesis of Spiro[1-azabicyclo[3.2.0]heptane] Frameworks via [3+2]-Cycloaddition. / Пронина, Юлия ; Филатов, А.С.; Shmakov, Stanislav V; Селиванов, Станислав Иванович; Крюкова, Мария Александровна; Спиридонова, Дарья Валерьевна; Поняев, Александр; Степаков, Александр Владимирович; Бойцов, Виталий Михайлович.

In: Journal of Organic Chemistry, Vol. 90, No. 14, 27.03.2025, p. 4926-4945.

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

Harvard

Пронина, Ю, Филатов, АС, Shmakov, SV, Селиванов, СИ, Крюкова, МА, Спиридонова, ДВ, Поняев, А, Степаков, АВ & Бойцов, ВМ 2025, 'Highly Efficient Synthesis of Spiro[1-azabicyclo[3.2.0]heptane] Frameworks via [3+2]-Cycloaddition', Journal of Organic Chemistry, vol. 90, no. 14, pp. 4926-4945. https://doi.org/10.1021/acs.joc.4c03183

APA

Пронина, Ю., Филатов, А. С., Shmakov, S. V., Селиванов, С. И., Крюкова, М. А., Спиридонова, Д. В., Поняев, А., Степаков, А. В., & Бойцов, В. М. (2025). Highly Efficient Synthesis of Spiro[1-azabicyclo[3.2.0]heptane] Frameworks via [3+2]-Cycloaddition. Journal of Organic Chemistry, 90(14), 4926-4945. https://doi.org/10.1021/acs.joc.4c03183

Vancouver

Пронина Ю, Филатов АС, Shmakov SV, Селиванов СИ, Крюкова МА, Спиридонова ДВ et al. Highly Efficient Synthesis of Spiro[1-azabicyclo[3.2.0]heptane] Frameworks via [3+2]-Cycloaddition. Journal of Organic Chemistry. 2025 Mar 27;90(14):4926-4945. https://doi.org/10.1021/acs.joc.4c03183

Author

Пронина, Юлия ; Филатов, А.С. ; Shmakov, Stanislav V ; Селиванов, Станислав Иванович ; Крюкова, Мария Александровна ; Спиридонова, Дарья Валерьевна ; Поняев, Александр ; Степаков, Александр Владимирович ; Бойцов, Виталий Михайлович. / Highly Efficient Synthesis of Spiro[1-azabicyclo[3.2.0]heptane] Frameworks via [3+2]-Cycloaddition. In: Journal of Organic Chemistry. 2025 ; Vol. 90, No. 14. pp. 4926-4945.

BibTeX

@article{4307c05c38324b3c825d76b6bdb15d03,
title = "Highly Efficient Synthesis of Spiro[1-azabicyclo[3.2.0]heptane] Frameworks via [3+2]-Cycloaddition",
abstract = "An efficient one-pot three-component [3 + 2]-cycloaddition reaction of azomethine ylides, generated in situ from isatins and azetidine-2-carboxylic acid, with different maleimides and itaconimides has been investigated. These reactions afford the corresponding spiro and dispiro[1-azabicyclo[3.2.0]heptanes] in moderate to high yields (up to 93%) with moderate to excellent diastereoselectivities and excellent regioselectivities under mild conditions. The method provides a simple route to the stereoselective synthesis of new polyheterocyclic systems such as 3-spiro[1-azabicyclo[3.2.0]heptane]oxindoles spiro-conjugated or fused to a succinimide moiety. The observed diastereo- and regioselectivity of cycloaddition reactions is reasoned by DFT studies. The antiproliferative effect of the synthesized compounds against cancer cell lines was assessed.",
author = "Юлия Пронина and А.С. Филатов and Shmakov, {Stanislav V} and Селиванов, {Станислав Иванович} and Крюкова, {Мария Александровна} and Спиридонова, {Дарья Валерьевна} and Александр Поняев and Степаков, {Александр Владимирович} and Бойцов, {Виталий Михайлович}",
year = "2025",
month = mar,
day = "27",
doi = "10.1021/acs.joc.4c03183",
language = "English",
volume = "90",
pages = "4926--4945",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "14",

}

RIS

TY - JOUR

T1 - Highly Efficient Synthesis of Spiro[1-azabicyclo[3.2.0]heptane] Frameworks via [3+2]-Cycloaddition

AU - Пронина, Юлия

AU - Филатов, А.С.

AU - Shmakov, Stanislav V

AU - Селиванов, Станислав Иванович

AU - Крюкова, Мария Александровна

AU - Спиридонова, Дарья Валерьевна

AU - Поняев, Александр

AU - Степаков, Александр Владимирович

AU - Бойцов, Виталий Михайлович

PY - 2025/3/27

Y1 - 2025/3/27

N2 - An efficient one-pot three-component [3 + 2]-cycloaddition reaction of azomethine ylides, generated in situ from isatins and azetidine-2-carboxylic acid, with different maleimides and itaconimides has been investigated. These reactions afford the corresponding spiro and dispiro[1-azabicyclo[3.2.0]heptanes] in moderate to high yields (up to 93%) with moderate to excellent diastereoselectivities and excellent regioselectivities under mild conditions. The method provides a simple route to the stereoselective synthesis of new polyheterocyclic systems such as 3-spiro[1-azabicyclo[3.2.0]heptane]oxindoles spiro-conjugated or fused to a succinimide moiety. The observed diastereo- and regioselectivity of cycloaddition reactions is reasoned by DFT studies. The antiproliferative effect of the synthesized compounds against cancer cell lines was assessed.

AB - An efficient one-pot three-component [3 + 2]-cycloaddition reaction of azomethine ylides, generated in situ from isatins and azetidine-2-carboxylic acid, with different maleimides and itaconimides has been investigated. These reactions afford the corresponding spiro and dispiro[1-azabicyclo[3.2.0]heptanes] in moderate to high yields (up to 93%) with moderate to excellent diastereoselectivities and excellent regioselectivities under mild conditions. The method provides a simple route to the stereoselective synthesis of new polyheterocyclic systems such as 3-spiro[1-azabicyclo[3.2.0]heptane]oxindoles spiro-conjugated or fused to a succinimide moiety. The observed diastereo- and regioselectivity of cycloaddition reactions is reasoned by DFT studies. The antiproliferative effect of the synthesized compounds against cancer cell lines was assessed.

UR - https://www.mendeley.com/catalogue/1e22446e-cb22-34d7-98fc-4e53bc251a4c/

U2 - 10.1021/acs.joc.4c03183

DO - 10.1021/acs.joc.4c03183

M3 - Article

VL - 90

SP - 4926

EP - 4945

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 14

ER -

ID: 137053591