Organocatalytic alkylation and photoorganocatalyst-free acylation of azomethine imines by Hantzsch esters under blue LED light

A synthetic method to prepare 1-alkyl-substituted-pyrazolidin-3-ones efficiently that relies on the 4CzPN-mediated alkylation of azomethine imines by 4-alkyl-substituted-1,4-dihydropyridines (DHPs) under blue light emitting diode (LED) light ( λ max = 456 nm) is reported. An approach that exploits t...

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Bibliographic Details
Published in:New journal of chemistry 2023-10, Vol.47 (42), p.19421-19427
Main Authors: Li, Jiacheng, Phetcharawetch, Jongkonporn, Qi, Minghao, Kyne, Sara Helen, Kuhakarn, Chutima, Zhong, Bingwei, Chan, Philip Wai Hong
Format: Article
Language:English
Subjects:
Acylation
Alkylation
Esters
Functional groups
Imines
Light emitting diodes
Room temperature
Substitutes
Substrates
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Summary:A synthetic method to prepare 1-alkyl-substituted-pyrazolidin-3-ones efficiently that relies on the 4CzPN-mediated alkylation of azomethine imines by 4-alkyl-substituted-1,4-dihydropyridines (DHPs) under blue light emitting diode (LED) light ( λ max = 456 nm) is reported. An approach that exploits the ability of blue LED light to initiate the acylation of the imine substrate by 4-acyl-substituted-DHPs to give 1-acyl-substituted-pyrazolidin-3-ones is also presented. Achieved under mild reaction conditions at room temperature, the synthetic protocol was shown to tolerate a broad range of functional groups to afford the corresponding 1-substituted-pyrazolidin-3-ones in yields up to 99%. Photoorganocatalytic alkylation of azomethine imines by 4-alkyl- and 4-acyl-substituted Hantzsch esters under blue LED light to give 1-alkyl- and 1-acyl-substituted-pyrazolidin-3-ones.
ISSN:1144-0546
1369-9261
DOI:10.1039/d3nj03780k