Visible-Light-Mediated α-Amino Alkylation of Azomethine Imines: An Approach to N-(β-Aminoalkyl)pyrazolidinones
Publication type: Journal Article
Publication date: 2020-09-28
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
32985192
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Herein, a mild and robust photocatalytic protocol for the combination of amino and pyrazolidinone functionalities through a radical α-amino alkylation of azomethine iminium ions is demonstrated. This method presents a high functional group tolerance providing direct access to a large family of N-(β-aminoalkyl)pyrazolidinones in good to excellent yields, including the late-stage incorporation of the pyrazolidinone moiety to pharmaceutical ingredients. We propose a plausible scenario for the C-C bond-forming step which involves radical addition followed by a spin-center-shift event.
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Metrics
31
Total citations:
31
Citations from 2025:
5
(16.13%)
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Matsuo B. T., Menezes Correia J. T., Paixao M. Visible-Light-Mediated α-Amino Alkylation of Azomethine Imines: An Approach to N-(β-Aminoalkyl)pyrazolidinones // Organic Letters. 2020. Vol. 22. No. 20. pp. 7891-7896.
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Matsuo B. T., Menezes Correia J. T., Paixao M. Visible-Light-Mediated α-Amino Alkylation of Azomethine Imines: An Approach to N-(β-Aminoalkyl)pyrazolidinones // Organic Letters. 2020. Vol. 22. No. 20. pp. 7891-7896.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.0c02821
UR - https://doi.org/10.1021/acs.orglett.0c02821
TI - Visible-Light-Mediated α-Amino Alkylation of Azomethine Imines: An Approach to N-(β-Aminoalkyl)pyrazolidinones
T2 - Organic Letters
AU - Matsuo, Bianca T
AU - Menezes Correia, José Tiago
AU - Paixao, Marcio
PY - 2020
DA - 2020/09/28
PB - American Chemical Society (ACS)
SP - 7891-7896
IS - 20
VL - 22
PMID - 32985192
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2020_Matsuo,
author = {Bianca T Matsuo and José Tiago Menezes Correia and Marcio Paixao},
title = {Visible-Light-Mediated α-Amino Alkylation of Azomethine Imines: An Approach to N-(β-Aminoalkyl)pyrazolidinones},
journal = {Organic Letters},
year = {2020},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.orglett.0c02821},
number = {20},
pages = {7891--7896},
doi = {10.1021/acs.orglett.0c02821}
}
Cite this
MLA
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Matsuo, Bianca T., et al. “Visible-Light-Mediated α-Amino Alkylation of Azomethine Imines: An Approach to N-(β-Aminoalkyl)pyrazolidinones.” Organic Letters, vol. 22, no. 20, Sep. 2020, pp. 7891-7896. https://doi.org/10.1021/acs.orglett.0c02821.