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

Jiacheng Li, Jongkonporn Phetcharawetch, Minghao Qi, Sara Helen Kyne, Chutima Kuhakarn, Bingwei Zhong, Philip Wai Hong Chan

Research output: Contribution to journalArticleResearchpeer-review

3 Citations (Scopus)

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%.

Original languageEnglish
Pages (from-to)19421-19427
Number of pages7
JournalNew Journal of Chemistry
Volume47
Issue number42
DOIs
Publication statusPublished - 14 Nov 2023

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