Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole–Isoxazole Dyads: Synthesis of Nonfused 1H-1,3-Diazepines
Gleb D Titov
1
,
Svetlana V. Urusova
1
,
Publication type: Journal Article
Publication date: 2024-09-06
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
39240763
Abstract
A 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.
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Total citations:
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Citations from 2024:
6
(100%)
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Titov G. D. et al. Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole–Isoxazole Dyads: Synthesis of Nonfused 1H-1,3-Diazepines // Organic Letters. 2024. Vol. 26. No. 37. pp. 7828-7833.
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Titov G. D., Bunev A. S., Urusova S. V., Novikov M. S., Khlebnikov A. F., Rostovskii N. V. Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole–Isoxazole Dyads: Synthesis of Nonfused 1H-1,3-Diazepines // Organic Letters. 2024. Vol. 26. No. 37. pp. 7828-7833.
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TY - JOUR
DO - 10.1021/acs.orglett.4c02588
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.4c02588
TI - Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole–Isoxazole Dyads: Synthesis of Nonfused 1H-1,3-Diazepines
T2 - Organic Letters
AU - Titov, Gleb D
AU - Bunev, Alexander S.
AU - Urusova, Svetlana V.
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
AU - Rostovskii, Nikolai V
PY - 2024
DA - 2024/09/06
PB - American Chemical Society (ACS)
SP - 7828-7833
IS - 37
VL - 26
PMID - 39240763
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2024_Titov,
author = {Gleb D Titov and Alexander S. Bunev and Svetlana V. Urusova and Mikhail S. Novikov and Alexander F Khlebnikov and Nikolai V Rostovskii},
title = {Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole–Isoxazole Dyads: Synthesis of Nonfused 1H-1,3-Diazepines},
journal = {Organic Letters},
year = {2024},
volume = {26},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c02588},
number = {37},
pages = {7828--7833},
doi = {10.1021/acs.orglett.4c02588}
}
Cite this
MLA
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Titov, Gleb D., et al. “Rhodium-Catalyzed Double Dearomatization of 1,2,3-Triazole–Isoxazole Dyads: Synthesis of Nonfused 1H-1,3-Diazepines.” Organic Letters, vol. 26, no. 37, Sep. 2024, pp. 7828-7833. https://pubs.acs.org/doi/10.1021/acs.orglett.4c02588.