Phosphine-Mediated Redox Cyclization of 1-(2-Nitroaryl)prop-2-ynones to 3-Hydroxyquinolin-4-ones: Formal Intramolecular Oxyamination of α,β-Ynones
Publication type: Journal Article
Publication date: 2022-10-13
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
36226855
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
3-Hydroxyquinoline-4(1H)-ones (3HQs) are privileged structural motifs. The current methods for their synthesis necessitate strongly acidic or basic conditions, which hamper the generality and practicality. Here, we describe phosphine-mediated redox transformation of easily accessible 1-(2-nitroaryl)prop-2-ynones to 3HQs. Besides establishing a new entry to the synthesis of 3HQs under neutral conditions, this method is the first formal intramolecular oxyamination of α,β-ynones. The synthetic utility of this method is demonstrated in the total synthesis of japonine, its analogs, and rare quinoline derivatives.
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Total citations:
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Citations from 2024:
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Dutta L., Ramasastry S. Phosphine-Mediated Redox Cyclization of 1-(2-Nitroaryl)prop-2-ynones to 3-Hydroxyquinolin-4-ones: Formal Intramolecular Oxyamination of α,β-Ynones // Organic Letters. 2022. Vol. 24. No. 41. pp. 7665-7670.
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Dutta L., Ramasastry S. Phosphine-Mediated Redox Cyclization of 1-(2-Nitroaryl)prop-2-ynones to 3-Hydroxyquinolin-4-ones: Formal Intramolecular Oxyamination of α,β-Ynones // Organic Letters. 2022. Vol. 24. No. 41. pp. 7665-7670.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.2c03232
UR - https://doi.org/10.1021/acs.orglett.2c03232
TI - Phosphine-Mediated Redox Cyclization of 1-(2-Nitroaryl)prop-2-ynones to 3-Hydroxyquinolin-4-ones: Formal Intramolecular Oxyamination of α,β-Ynones
T2 - Organic Letters
AU - Dutta, Lona
AU - Ramasastry, S.S.V.
PY - 2022
DA - 2022/10/13
PB - American Chemical Society (ACS)
SP - 7665-7670
IS - 41
VL - 24
PMID - 36226855
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2022_Dutta,
author = {Lona Dutta and S.S.V. Ramasastry},
title = {Phosphine-Mediated Redox Cyclization of 1-(2-Nitroaryl)prop-2-ynones to 3-Hydroxyquinolin-4-ones: Formal Intramolecular Oxyamination of α,β-Ynones},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.orglett.2c03232},
number = {41},
pages = {7665--7670},
doi = {10.1021/acs.orglett.2c03232}
}
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MLA
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Dutta, Lona, and S.S.V. Ramasastry. “Phosphine-Mediated Redox Cyclization of 1-(2-Nitroaryl)prop-2-ynones to 3-Hydroxyquinolin-4-ones: Formal Intramolecular Oxyamination of α,β-Ynones.” Organic Letters, vol. 24, no. 41, Oct. 2022, pp. 7665-7670. https://doi.org/10.1021/acs.orglett.2c03232.