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3-Diazopiperidine-2,4-diones as Convenient Precursors to Rare Polysubstituted Spiro Bis-β,γ-lactams and 2-Oxopyrrolidine-3-carboxylic Acid Derivatives via the Thermally Promoted Wolff Rearrangement. / Левашова, Екатерина Юрьевна; Адамчик, Мария Александровна; Рязанцев, Михаил Николаевич; Дарьин, Дмитрий Викторович.

In: Journal of Organic Chemistry, Vol. 89, No. 22, 25.10.2024.

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

Harvard

Левашова, ЕЮ, Адамчик, МА, Рязанцев, МН & Дарьин, ДВ 2024, '3-Diazopiperidine-2,4-diones as Convenient Precursors to Rare Polysubstituted Spiro Bis-β,γ-lactams and 2-Oxopyrrolidine-3-carboxylic Acid Derivatives via the Thermally Promoted Wolff Rearrangement', Journal of Organic Chemistry, vol. 89, no. 22. https://doi.org/10.1021/acs.joc.4c02017

APA

Левашова, Е. Ю., Адамчик, М. А., Рязанцев, М. Н., & Дарьин, Д. В. (2024). 3-Diazopiperidine-2,4-diones as Convenient Precursors to Rare Polysubstituted Spiro Bis-β,γ-lactams and 2-Oxopyrrolidine-3-carboxylic Acid Derivatives via the Thermally Promoted Wolff Rearrangement. Journal of Organic Chemistry, 89(22). https://doi.org/10.1021/acs.joc.4c02017

Vancouver

Левашова ЕЮ, Адамчик МА, Рязанцев МН, Дарьин ДВ. 3-Diazopiperidine-2,4-diones as Convenient Precursors to Rare Polysubstituted Spiro Bis-β,γ-lactams and 2-Oxopyrrolidine-3-carboxylic Acid Derivatives via the Thermally Promoted Wolff Rearrangement. Journal of Organic Chemistry. 2024 Oct 25;89(22). https://doi.org/10.1021/acs.joc.4c02017

Author

Левашова, Екатерина Юрьевна ; Адамчик, Мария Александровна ; Рязанцев, Михаил Николаевич ; Дарьин, Дмитрий Викторович. / 3-Diazopiperidine-2,4-diones as Convenient Precursors to Rare Polysubstituted Spiro Bis-β,γ-lactams and 2-Oxopyrrolidine-3-carboxylic Acid Derivatives via the Thermally Promoted Wolff Rearrangement. In: Journal of Organic Chemistry. 2024 ; Vol. 89, No. 22.

BibTeX

@article{4b8dec22532245ac858ad4be3b6dd6da,
title = "3-Diazopiperidine-2,4-diones as Convenient Precursors to Rare Polysubstituted Spiro Bis-β,γ-lactams and 2-Oxopyrrolidine-3-carboxylic Acid Derivatives via the Thermally Promoted Wolff Rearrangement",
abstract = "Herein, we describe a diastereoselective and straightforward synthetic approach to polysubstituted spirocyclic bis-lactams bearing both β- and γ-lactam cores with diverse substitution patterns. The method developed is based on a microwave-assisted Wolff rearrangement/Staudinger [2 + 2] cycloaddition sequence involving 3-diazopiperidine-2,4-diones and imines. The corresponding reaction tolerates a wide range of functionalities in both substrates, giving the target bis-lactams in generally high yields. The synthetic utility of the thermally promoted Wolff rearrangement has been extended to the interaction of 3-diazopiperidine-2,4-dione-derived ketenes with various nucleophiles leading to derivatives of 2-oxopyrrolidine-3-carboxylic acids. Our findings potentially pave an avenue for designing new compounds with a high degree of medicinal relevance by means of the processes studied.",
author = "Левашова, {Екатерина Юрьевна} and Адамчик, {Мария Александровна} and Рязанцев, {Михаил Николаевич} and Дарьин, {Дмитрий Викторович}",
year = "2024",
month = oct,
day = "25",
doi = "10.1021/acs.joc.4c02017",
language = "English",
volume = "89",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "22",

}

RIS

TY - JOUR

T1 - 3-Diazopiperidine-2,4-diones as Convenient Precursors to Rare Polysubstituted Spiro Bis-β,γ-lactams and 2-Oxopyrrolidine-3-carboxylic Acid Derivatives via the Thermally Promoted Wolff Rearrangement

AU - Левашова, Екатерина Юрьевна

AU - Адамчик, Мария Александровна

AU - Рязанцев, Михаил Николаевич

AU - Дарьин, Дмитрий Викторович

PY - 2024/10/25

Y1 - 2024/10/25

N2 - Herein, we describe a diastereoselective and straightforward synthetic approach to polysubstituted spirocyclic bis-lactams bearing both β- and γ-lactam cores with diverse substitution patterns. The method developed is based on a microwave-assisted Wolff rearrangement/Staudinger [2 + 2] cycloaddition sequence involving 3-diazopiperidine-2,4-diones and imines. The corresponding reaction tolerates a wide range of functionalities in both substrates, giving the target bis-lactams in generally high yields. The synthetic utility of the thermally promoted Wolff rearrangement has been extended to the interaction of 3-diazopiperidine-2,4-dione-derived ketenes with various nucleophiles leading to derivatives of 2-oxopyrrolidine-3-carboxylic acids. Our findings potentially pave an avenue for designing new compounds with a high degree of medicinal relevance by means of the processes studied.

AB - Herein, we describe a diastereoselective and straightforward synthetic approach to polysubstituted spirocyclic bis-lactams bearing both β- and γ-lactam cores with diverse substitution patterns. The method developed is based on a microwave-assisted Wolff rearrangement/Staudinger [2 + 2] cycloaddition sequence involving 3-diazopiperidine-2,4-diones and imines. The corresponding reaction tolerates a wide range of functionalities in both substrates, giving the target bis-lactams in generally high yields. The synthetic utility of the thermally promoted Wolff rearrangement has been extended to the interaction of 3-diazopiperidine-2,4-dione-derived ketenes with various nucleophiles leading to derivatives of 2-oxopyrrolidine-3-carboxylic acids. Our findings potentially pave an avenue for designing new compounds with a high degree of medicinal relevance by means of the processes studied.

UR - https://www.mendeley.com/catalogue/28ae401e-4e1b-3f34-9236-6962dbe56eab/

U2 - 10.1021/acs.joc.4c02017

DO - 10.1021/acs.joc.4c02017

M3 - Article

VL - 89

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 22

ER -

ID: 126591146