AI Article Synopsis
- A new pyridine-catalyzed four-component reaction has been developed that combines aromatic aldehydes, malononitrile/cyanoacetates, Morita-Baylis-Hillman carbonates, and alcohols in a single process.
- This reaction involves a unique mechanism that includes solvent effects and follows a sequence of Knoevenagel condensation, oxa-Michael addition, and S2' substitution.
- The method yields diverse functionalized compounds, such as chain alkylbenzenes and dihydroquinolinones, with a modifiable all-carbon quaternary center by simply adjusting the electron-withdrawing groups involved.
Article Abstract
An efficient pyridine-catalyzed chemoselective four-component cascade reaction of aromatic aldehydes, malononitrile/cyanoacetates, Morita-Baylis-Hillman (MBH) carbonates, and alcohols has been established. This one-pot reaction progressed in an unusual reaction with solvent participation via a Knoevenagel condensation/oxa-Michael addition/S2' substitution sequence. This method allowed for facile access to an array of functionalized chain alkylbenzenes and dihydroquinolinones bearing one all-carbon quaternary center in moderate to excellent yields. It is worth noting that the configuration of the all-carbon quaternary center could be modulated by changing only the electron-withdrawing groups via a tandem reduction/cyclization reaction.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.4c02612 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!