Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling
Publication type: Journal Article
Publication date: 2021-08-30
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
A convenient approach to assemble 1,2,3-triazole-fused 4H-3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C–O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C–I bond was achieved by the use of Na2CO3 in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.
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Total citations:
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Citations from 2024:
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(37%)
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Kotovshchikov Y. N. et al. Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling // Synthesis. 2021. Vol. 54. No. 02. pp. 369-377.
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Kotovshchikov Y. N., Kotovshchikov Y. N., Latyshev G. V., Lukashev N. V., Beletskaya I. P. Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling // Synthesis. 2021. Vol. 54. No. 02. pp. 369-377.
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RIS
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TY - JOUR
DO - 10.1055/a-1623-2333
UR - https://doi.org/10.1055/a-1623-2333
TI - Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling
T2 - Synthesis
AU - Kotovshchikov, Yury N
AU - Kotovshchikov, Yury N
AU - Latyshev, Gennadij V
AU - Lukashev, Nikolay V
AU - Beletskaya, Irina P.
PY - 2021
DA - 2021/08/30
PB - Georg Thieme Verlag KG
SP - 369-377
IS - 02
VL - 54
SN - 0039-7881
SN - 1437-210X
ER -
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BibTex (up to 50 authors)
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@article{2021_Kotovshchikov,
author = {Yury N Kotovshchikov and Yury N Kotovshchikov and Gennadij V Latyshev and Nikolay V Lukashev and Irina P. Beletskaya},
title = {Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling},
journal = {Synthesis},
year = {2021},
volume = {54},
publisher = {Georg Thieme Verlag KG},
month = {aug},
url = {https://doi.org/10.1055/a-1623-2333},
number = {02},
pages = {369--377},
doi = {10.1055/a-1623-2333}
}
Cite this
MLA
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Kotovshchikov, Yury N., et al. “Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling.” Synthesis, vol. 54, no. 02, Aug. 2021, pp. 369-377. https://doi.org/10.1055/a-1623-2333.