Organocatalytic alkylation and photoorganocatalyst-free acylation of azomethine imines by Hantzsch esters under blue LED light
Issued Date
2023-01-01
Resource Type
ISSN
11440546
eISSN
13699261
Scopus ID
2-s2.0-85174510986
Journal Title
New Journal of Chemistry
Rights Holder(s)
SCOPUS
Bibliographic Citation
New Journal of Chemistry (2023)
Suggested Citation
Li J., Phetcharawetch J., Qi M., Kyne S.H., Kuhakarn C., Zhong B., Chan P.W.H. Organocatalytic alkylation and photoorganocatalyst-free acylation of azomethine imines by Hantzsch esters under blue LED light. New Journal of Chemistry (2023). doi:10.1039/d3nj03780k Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/90820
Title
Organocatalytic alkylation and photoorganocatalyst-free acylation of azomethine imines by Hantzsch esters under blue LED light
Other Contributor(s)
Abstract
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 (λmax = 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%.