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A Precise Synthetic Toolbox: H-Bond-Assisted Quadruple Reactivity of o-Dimethylaminoaryloximes. / Цыбулин, Семен Валерьевич; Мешалкин, Степан Алексеевич; Тонкоглазова, Дарья Игоревна; Бардаков, Виктор Геннадьевич; Пожарский, Александр Федорович; Антонов, Александр Сергеевич.

в: The Journal of organic chemistry, Том 90, № 12, 28.03.2025, стр. 4374–4381.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Цыбулин, СВ, Мешалкин, СА, Тонкоглазова, ДИ, Бардаков, ВГ, Пожарский, АФ & Антонов, АС 2025, 'A Precise Synthetic Toolbox: H-Bond-Assisted Quadruple Reactivity of o-Dimethylaminoaryloximes', The Journal of organic chemistry, Том. 90, № 12, стр. 4374–4381. https://doi.org/10.1021/acs.joc.5c00207

APA

Цыбулин, С. В., Мешалкин, С. А., Тонкоглазова, Д. И., Бардаков, В. Г., Пожарский, А. Ф., & Антонов, А. С. (2025). A Precise Synthetic Toolbox: H-Bond-Assisted Quadruple Reactivity of o-Dimethylaminoaryloximes. The Journal of organic chemistry, 90(12), 4374–4381. https://doi.org/10.1021/acs.joc.5c00207

Vancouver

Цыбулин СВ, Мешалкин СА, Тонкоглазова ДИ, Бардаков ВГ, Пожарский АФ, Антонов АС. A Precise Synthetic Toolbox: H-Bond-Assisted Quadruple Reactivity of o-Dimethylaminoaryloximes. The Journal of organic chemistry. 2025 Март 28;90(12):4374–4381. https://doi.org/10.1021/acs.joc.5c00207

Author

Цыбулин, Семен Валерьевич ; Мешалкин, Степан Алексеевич ; Тонкоглазова, Дарья Игоревна ; Бардаков, Виктор Геннадьевич ; Пожарский, Александр Федорович ; Антонов, Александр Сергеевич. / A Precise Synthetic Toolbox: H-Bond-Assisted Quadruple Reactivity of o-Dimethylaminoaryloximes. в: The Journal of organic chemistry. 2025 ; Том 90, № 12. стр. 4374–4381.

BibTeX

@article{c2a513bb0f8744858c9c74ca8b14ecfe,
title = "A Precise Synthetic Toolbox: H-Bond-Assisted Quadruple Reactivity of o-Dimethylaminoaryloximes",
abstract = "Non-covalent interactions are a highly promising tool for the development of transition-metal-free chemospecific synthetic transformations. Here, we demonstrate the implementation of non-covalent interactions as a simple, precise, and flexible synthetic toolbox, allowing the controlled transformation of o-dimethylaminoaryloximes into nitriles and hard-to-reach nitrogen heterocycles under mild conditions. This diverse reactivity is activated via hydrogen bonding and facilitated via the {"}buttressing effect{"} of the substituents next to the NMe 2 group. All transformations require only simple and easily available acids and solvents, which generally provide precise control over the direction of the reaction, allowing the selective synthesis of nitriles, fused pyrazoles, isoxazoles, and pyrroles. ",
author = "Цыбулин, {Семен Валерьевич} and Мешалкин, {Степан Алексеевич} and Тонкоглазова, {Дарья Игоревна} and Бардаков, {Виктор Геннадьевич} and Пожарский, {Александр Федорович} and Антонов, {Александр Сергеевич}",
year = "2025",
month = mar,
day = "28",
doi = "10.1021/acs.joc.5c00207",
language = "English",
volume = "90",
pages = "4374–4381",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "12",

}

RIS

TY - JOUR

T1 - A Precise Synthetic Toolbox: H-Bond-Assisted Quadruple Reactivity of o-Dimethylaminoaryloximes

AU - Цыбулин, Семен Валерьевич

AU - Мешалкин, Степан Алексеевич

AU - Тонкоглазова, Дарья Игоревна

AU - Бардаков, Виктор Геннадьевич

AU - Пожарский, Александр Федорович

AU - Антонов, Александр Сергеевич

PY - 2025/3/28

Y1 - 2025/3/28

N2 - Non-covalent interactions are a highly promising tool for the development of transition-metal-free chemospecific synthetic transformations. Here, we demonstrate the implementation of non-covalent interactions as a simple, precise, and flexible synthetic toolbox, allowing the controlled transformation of o-dimethylaminoaryloximes into nitriles and hard-to-reach nitrogen heterocycles under mild conditions. This diverse reactivity is activated via hydrogen bonding and facilitated via the "buttressing effect" of the substituents next to the NMe 2 group. All transformations require only simple and easily available acids and solvents, which generally provide precise control over the direction of the reaction, allowing the selective synthesis of nitriles, fused pyrazoles, isoxazoles, and pyrroles.

AB - Non-covalent interactions are a highly promising tool for the development of transition-metal-free chemospecific synthetic transformations. Here, we demonstrate the implementation of non-covalent interactions as a simple, precise, and flexible synthetic toolbox, allowing the controlled transformation of o-dimethylaminoaryloximes into nitriles and hard-to-reach nitrogen heterocycles under mild conditions. This diverse reactivity is activated via hydrogen bonding and facilitated via the "buttressing effect" of the substituents next to the NMe 2 group. All transformations require only simple and easily available acids and solvents, which generally provide precise control over the direction of the reaction, allowing the selective synthesis of nitriles, fused pyrazoles, isoxazoles, and pyrroles.

UR - https://www.mendeley.com/catalogue/0d5cce9c-d4bd-340f-b7fb-43f089d18fb7/

U2 - 10.1021/acs.joc.5c00207

DO - 10.1021/acs.joc.5c00207

M3 - Article

C2 - 40080825

VL - 90

SP - 4374

EP - 4381

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 12

ER -

ID: 134552749