Standard

Synthesis of Azirinyl Ethynyl Ketones and Their Use in the Preparation C(O)CCR-Substituted NH-Pyrroles/NH-Imidazoles and Azole−Azine/Azole−Azole Heterocyclic Hybrids. / Галенко, Екатерина Евгениевна; Бодунов, Владимир Андреевич; Таишев, Артур Эдуардович; Новиков, Михаил Сергеевич; Хлебников, Александр Феодосиевич.

In: Journal of Organic Chemistry, Vol. 90, 25.02.2025.

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

Harvard

Галенко, ЕЕ, Бодунов, ВА, Таишев, АЭ, Новиков, МС & Хлебников, АФ 2025, 'Synthesis of Azirinyl Ethynyl Ketones and Their Use in the Preparation C(O)CCR-Substituted NH-Pyrroles/NH-Imidazoles and Azole−Azine/Azole−Azole Heterocyclic Hybrids.', Journal of Organic Chemistry, vol. 90. https://doi.org/10.1021/acs.joc.4c02970

APA

Галенко, Е. Е., Бодунов, В. А., Таишев, А. Э., Новиков, М. С., & Хлебников, А. Ф. (2025). Synthesis of Azirinyl Ethynyl Ketones and Their Use in the Preparation C(O)CCR-Substituted NH-Pyrroles/NH-Imidazoles and Azole−Azine/Azole−Azole Heterocyclic Hybrids. Journal of Organic Chemistry, 90. https://doi.org/10.1021/acs.joc.4c02970

Vancouver

Галенко ЕЕ, Бодунов ВА, Таишев АЭ, Новиков МС, Хлебников АФ. Synthesis of Azirinyl Ethynyl Ketones and Their Use in the Preparation C(O)CCR-Substituted NH-Pyrroles/NH-Imidazoles and Azole−Azine/Azole−Azole Heterocyclic Hybrids. Journal of Organic Chemistry. 2025 Feb 25;90. https://doi.org/10.1021/acs.joc.4c02970

Author

Галенко, Екатерина Евгениевна ; Бодунов, Владимир Андреевич ; Таишев, Артур Эдуардович ; Новиков, Михаил Сергеевич ; Хлебников, Александр Феодосиевич. / Synthesis of Azirinyl Ethynyl Ketones and Their Use in the Preparation C(O)CCR-Substituted NH-Pyrroles/NH-Imidazoles and Azole−Azine/Azole−Azole Heterocyclic Hybrids. In: Journal of Organic Chemistry. 2025 ; Vol. 90.

BibTeX

@article{daac42ddfefc4b27a9c2bb8deb1dda73,
title = "Synthesis of Azirinyl Ethynyl Ketones and Their Use in the Preparation C(O)CCR-Substituted NH-Pyrroles/NH-Imidazoles and Azole−Azine/Azole−Azole Heterocyclic Hybrids.",
abstract = "Azirinyl-substituted conjugated ynones were first synthesized by the reaction of lithiated acetylenes with 2H-azirine-2-carbonyl chlorides. Azirinyl ethynyl ketones containing only a C(O)C≡CR substituent at position 2 of the azirine ring are good precursors for obtaining α-C(O)C≡CR substituted NH-pyrroles and 5-[C(O)C≡CR]-substituted NH-imidazoles, reacting selectively only at the azirine moiety with 1,3-diketones and arylamidines, respectively. Various N-heterocyclic hybrids (pyrrole-pyrimidine, imidazole-pyrimidine, pyrrole-isoxazole, imidazole-isoxazole, pyrimidine-pyrrole-thiophene, pyrrole-pyrimidine-thiophene, imidazole-pyrimidine-thiophene, isoxazole-pyrrole-thiophene) have been prepared based on orthogonal or domino reactions of an azirine and C(O)C≡CR moieties of azirinyl ethynyl ketones.",
author = "Галенко, {Екатерина Евгениевна} and Бодунов, {Владимир Андреевич} and Таишев, {Артур Эдуардович} and Новиков, {Михаил Сергеевич} and Хлебников, {Александр Феодосиевич}",
year = "2025",
month = feb,
day = "25",
doi = "10.1021/acs.joc.4c02970",
language = "English",
volume = "90",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",

}

RIS

TY - JOUR

T1 - Synthesis of Azirinyl Ethynyl Ketones and Their Use in the Preparation C(O)CCR-Substituted NH-Pyrroles/NH-Imidazoles and Azole−Azine/Azole−Azole Heterocyclic Hybrids.

AU - Галенко, Екатерина Евгениевна

AU - Бодунов, Владимир Андреевич

AU - Таишев, Артур Эдуардович

AU - Новиков, Михаил Сергеевич

AU - Хлебников, Александр Феодосиевич

PY - 2025/2/25

Y1 - 2025/2/25

N2 - Azirinyl-substituted conjugated ynones were first synthesized by the reaction of lithiated acetylenes with 2H-azirine-2-carbonyl chlorides. Azirinyl ethynyl ketones containing only a C(O)C≡CR substituent at position 2 of the azirine ring are good precursors for obtaining α-C(O)C≡CR substituted NH-pyrroles and 5-[C(O)C≡CR]-substituted NH-imidazoles, reacting selectively only at the azirine moiety with 1,3-diketones and arylamidines, respectively. Various N-heterocyclic hybrids (pyrrole-pyrimidine, imidazole-pyrimidine, pyrrole-isoxazole, imidazole-isoxazole, pyrimidine-pyrrole-thiophene, pyrrole-pyrimidine-thiophene, imidazole-pyrimidine-thiophene, isoxazole-pyrrole-thiophene) have been prepared based on orthogonal or domino reactions of an azirine and C(O)C≡CR moieties of azirinyl ethynyl ketones.

AB - Azirinyl-substituted conjugated ynones were first synthesized by the reaction of lithiated acetylenes with 2H-azirine-2-carbonyl chlorides. Azirinyl ethynyl ketones containing only a C(O)C≡CR substituent at position 2 of the azirine ring are good precursors for obtaining α-C(O)C≡CR substituted NH-pyrroles and 5-[C(O)C≡CR]-substituted NH-imidazoles, reacting selectively only at the azirine moiety with 1,3-diketones and arylamidines, respectively. Various N-heterocyclic hybrids (pyrrole-pyrimidine, imidazole-pyrimidine, pyrrole-isoxazole, imidazole-isoxazole, pyrimidine-pyrrole-thiophene, pyrrole-pyrimidine-thiophene, imidazole-pyrimidine-thiophene, isoxazole-pyrrole-thiophene) have been prepared based on orthogonal or domino reactions of an azirine and C(O)C≡CR moieties of azirinyl ethynyl ketones.

UR - https://www.mendeley.com/catalogue/ea6f8f44-5a56-3d34-bfb0-8697adcf8020/

U2 - 10.1021/acs.joc.4c02970

DO - 10.1021/acs.joc.4c02970

M3 - Article

VL - 90

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

ER -

ID: 132485478