Standard

Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole−Isoxazole Dyads: Synthesis of Nonfused 1H‑1,3-Diazepines. / Ростовский, Николай Витальевич; Хлебников, Александр Феодосиевич; Новиков, Михаил Сергеевич; Титов, Глеб Денисович; Урусова, Светлана Владимировна; Бунев, Александр Сиясатович.

In: Organic Letters, Vol. 26, No. 37, 06.09.2024, p. 7828−7833.

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

Harvard

Ростовский, НВ, Хлебников, АФ, Новиков, МС, Титов, ГД, Урусова, СВ & Бунев, АС 2024, 'Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole−Isoxazole Dyads: Synthesis of Nonfused 1H‑1,3-Diazepines', Organic Letters, vol. 26, no. 37, pp. 7828−7833.

APA

Ростовский, Н. В., Хлебников, А. Ф., Новиков, М. С., Титов, Г. Д., Урусова, С. В., & Бунев, А. С. (2024). Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole−Isoxazole Dyads: Synthesis of Nonfused 1H‑1,3-Diazepines. Organic Letters, 26(37), 7828−7833.

Vancouver

Ростовский НВ, Хлебников АФ, Новиков МС, Титов ГД, Урусова СВ, Бунев АС. Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole−Isoxazole Dyads: Synthesis of Nonfused 1H‑1,3-Diazepines. Organic Letters. 2024 Sep 6;26(37):7828−7833.

Author

Ростовский, Николай Витальевич ; Хлебников, Александр Феодосиевич ; Новиков, Михаил Сергеевич ; Титов, Глеб Денисович ; Урусова, Светлана Владимировна ; Бунев, Александр Сиясатович. / Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole−Isoxazole Dyads: Synthesis of Nonfused 1H‑1,3-Diazepines. In: Organic Letters. 2024 ; Vol. 26, No. 37. pp. 7828−7833.

BibTeX

@article{c12e6aab2173441fbfa535bb3d14bd18,
title = "Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole−Isoxazole Dyads: Synthesis of Nonfused 1H‑1,3-Diazepines",
abstract = "double dearomatization of dyads consisting of 1-sulfonyl-1,2,3-triazoles and 3-aryl-5-methoxyisoxazoles was applied for the efficient synthesis of nonfused 1H-1,3-diazepines. The plausible mechanism of the cascade reaction includes transformation of the 1,2,3-triazole to rhodium azavinyl carbene, the Z-selective hydride shift to form the 1-azabuta-1,3-diene moiety, rhodium-catalyzed ring contraction of the isoxazole to azirine, and pseudopericyclic four-atom ring expansion of the azirine. The synthetic utility and antiproliferative activity of the 1,3-diazepines obtained have been demonstrated.",
author = "Ростовский, {Николай Витальевич} and Хлебников, {Александр Феодосиевич} and Новиков, {Михаил Сергеевич} and Титов, {Глеб Денисович} and Урусова, {Светлана Владимировна} and Бунев, {Александр Сиясатович}",
year = "2024",
month = sep,
day = "6",
language = "English",
volume = "26",
pages = "7828−7833",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "37",

}

RIS

TY - JOUR

T1 - Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole−Isoxazole Dyads: Synthesis of Nonfused 1H‑1,3-Diazepines

AU - Ростовский, Николай Витальевич

AU - Хлебников, Александр Феодосиевич

AU - Новиков, Михаил Сергеевич

AU - Титов, Глеб Денисович

AU - Урусова, Светлана Владимировна

AU - Бунев, Александр Сиясатович

PY - 2024/9/6

Y1 - 2024/9/6

N2 - double dearomatization of dyads consisting of 1-sulfonyl-1,2,3-triazoles and 3-aryl-5-methoxyisoxazoles was applied for the efficient synthesis of nonfused 1H-1,3-diazepines. The plausible mechanism of the cascade reaction includes transformation of the 1,2,3-triazole to rhodium azavinyl carbene, the Z-selective hydride shift to form the 1-azabuta-1,3-diene moiety, rhodium-catalyzed ring contraction of the isoxazole to azirine, and pseudopericyclic four-atom ring expansion of the azirine. The synthetic utility and antiproliferative activity of the 1,3-diazepines obtained have been demonstrated.

AB - double dearomatization of dyads consisting of 1-sulfonyl-1,2,3-triazoles and 3-aryl-5-methoxyisoxazoles was applied for the efficient synthesis of nonfused 1H-1,3-diazepines. The plausible mechanism of the cascade reaction includes transformation of the 1,2,3-triazole to rhodium azavinyl carbene, the Z-selective hydride shift to form the 1-azabuta-1,3-diene moiety, rhodium-catalyzed ring contraction of the isoxazole to azirine, and pseudopericyclic four-atom ring expansion of the azirine. The synthetic utility and antiproliferative activity of the 1,3-diazepines obtained have been demonstrated.

M3 - Article

VL - 26

SP - 7828−7833

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 37

ER -

ID: 126280301