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Utilizing Allenic Acids and Heterocyclic Diazo Compounds in the Synthesis of Polysubstituted Spirocyclic Butenolides and β-Methylidene 2-Furanones. / Малкова, Ксения Павловна; Татаринов, Илья Александрович; Кантин, Григорий Павлович; Дарьин, Дмитрий Викторович.

In: Journal of Organic Chemistry, Vol. 89, No. 4, 16.02.2024, p. 2782–2786.

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

Harvard

Малкова, КП, Татаринов, ИА, Кантин, ГП & Дарьин, ДВ 2024, 'Utilizing Allenic Acids and Heterocyclic Diazo Compounds in the Synthesis of Polysubstituted Spirocyclic Butenolides and β-Methylidene 2-Furanones', Journal of Organic Chemistry, vol. 89, no. 4, pp. 2782–2786. https://doi.org/10.1021/acs.joc.3c02474

APA

Малкова, К. П., Татаринов, И. А., Кантин, Г. П., & Дарьин, Д. В. (2024). Utilizing Allenic Acids and Heterocyclic Diazo Compounds in the Synthesis of Polysubstituted Spirocyclic Butenolides and β-Methylidene 2-Furanones. Journal of Organic Chemistry, 89(4), 2782–2786. https://doi.org/10.1021/acs.joc.3c02474

Vancouver

Малкова КП, Татаринов ИА, Кантин ГП, Дарьин ДВ. Utilizing Allenic Acids and Heterocyclic Diazo Compounds in the Synthesis of Polysubstituted Spirocyclic Butenolides and β-Methylidene 2-Furanones. Journal of Organic Chemistry. 2024 Feb 16;89(4):2782–2786. https://doi.org/10.1021/acs.joc.3c02474

Author

Малкова, Ксения Павловна ; Татаринов, Илья Александрович ; Кантин, Григорий Павлович ; Дарьин, Дмитрий Викторович. / Utilizing Allenic Acids and Heterocyclic Diazo Compounds in the Synthesis of Polysubstituted Spirocyclic Butenolides and β-Methylidene 2-Furanones. In: Journal of Organic Chemistry. 2024 ; Vol. 89, No. 4. pp. 2782–2786.

BibTeX

@article{a11bd5059d394b6b9ef0207f73662025,
title = "Utilizing Allenic Acids and Heterocyclic Diazo Compounds in the Synthesis of Polysubstituted Spirocyclic Butenolides and β-Methylidene 2-Furanones",
abstract = "Herein, we report a novel approach for the assembly of spirocyclic Δα,β-butenolides and β-methylidene 2-furanones via Rh(II)-catalyzed O-H insertion of heterocyclic diazo compounds into allenic acids followed by base-promoted cyclization. Utilizing various diazo heterocycles, including α-diazo homophthalimides, 3-diazo tetramic acids, and diazo oxindoles, diverse spirocyclic scaffolds were produced. The research revealed that the allenic acid substitution pattern is decisive for the product type, enabling extraordinary target compound switching between two types of spirocyclic 2-furanones with exo- and endocyclic C═C bonds.",
author = "Малкова, {Ксения Павловна} and Татаринов, {Илья Александрович} and Кантин, {Григорий Павлович} and Дарьин, {Дмитрий Викторович}",
note = "Funding Information: The authors are grateful to the Russian Science Foundation for financial support (Project Grant 20-13-00024). The authors thank the Research Centre for Magnetic Resonance, the Center for Chemical Analysis and Materials Research, and the Centre for X-ray Diffraction Methods of Saint Petersburg State University Research Park for obtaining the analytical data.",
year = "2024",
month = feb,
day = "16",
doi = "10.1021/acs.joc.3c02474",
language = "English",
volume = "89",
pages = "2782–2786",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "4",

}

RIS

TY - JOUR

T1 - Utilizing Allenic Acids and Heterocyclic Diazo Compounds in the Synthesis of Polysubstituted Spirocyclic Butenolides and β-Methylidene 2-Furanones

AU - Малкова, Ксения Павловна

AU - Татаринов, Илья Александрович

AU - Кантин, Григорий Павлович

AU - Дарьин, Дмитрий Викторович

N1 - Funding Information: The authors are grateful to the Russian Science Foundation for financial support (Project Grant 20-13-00024). The authors thank the Research Centre for Magnetic Resonance, the Center for Chemical Analysis and Materials Research, and the Centre for X-ray Diffraction Methods of Saint Petersburg State University Research Park for obtaining the analytical data.

PY - 2024/2/16

Y1 - 2024/2/16

N2 - Herein, we report a novel approach for the assembly of spirocyclic Δα,β-butenolides and β-methylidene 2-furanones via Rh(II)-catalyzed O-H insertion of heterocyclic diazo compounds into allenic acids followed by base-promoted cyclization. Utilizing various diazo heterocycles, including α-diazo homophthalimides, 3-diazo tetramic acids, and diazo oxindoles, diverse spirocyclic scaffolds were produced. The research revealed that the allenic acid substitution pattern is decisive for the product type, enabling extraordinary target compound switching between two types of spirocyclic 2-furanones with exo- and endocyclic C═C bonds.

AB - Herein, we report a novel approach for the assembly of spirocyclic Δα,β-butenolides and β-methylidene 2-furanones via Rh(II)-catalyzed O-H insertion of heterocyclic diazo compounds into allenic acids followed by base-promoted cyclization. Utilizing various diazo heterocycles, including α-diazo homophthalimides, 3-diazo tetramic acids, and diazo oxindoles, diverse spirocyclic scaffolds were produced. The research revealed that the allenic acid substitution pattern is decisive for the product type, enabling extraordinary target compound switching between two types of spirocyclic 2-furanones with exo- and endocyclic C═C bonds.

UR - https://www.mendeley.com/catalogue/ef678236-1427-3003-bab5-59865da9fdbe/

U2 - 10.1021/acs.joc.3c02474

DO - 10.1021/acs.joc.3c02474

M3 - Article

VL - 89

SP - 2782

EP - 2786

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 4

ER -

ID: 116543644