Next Article in Journal
Red Ginseng Marc Oil Inhibits iNOS and COX-2 via NFκB and p38 Pathways in LPS-Stimulated RAW 264.7 Macrophages
Next Article in Special Issue
New Advances in Titanium-Mediated Free Radical Reactions
Previous Article in Journal
Generation of the First Structure-Based Pharmacophore Model Containing a Selective “Zinc Binding Group” Feature to Identify Potential Glyoxalase-1 Inhibitors
Previous Article in Special Issue
Azide-Alkyne Huisgen [3+2] Cycloaddition Using CuO Nanoparticles
Molecules 2012, 17(12), 13759-13768; doi:10.3390/molecules171213759
Communication

Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides

,
 and
*
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC H3A 2K6, Canada
* Author to whom correspondence should be addressed.
Received: 25 October 2012 / Revised: 13 November 2012 / Accepted: 14 November 2012 / Published: 22 November 2012
(This article belongs to the Special Issue Transition Metals Catalysis)
Download PDF [289 KB, uploaded 18 June 2014]

Abstract

We describe the palladium-catalyzed multicomponent synthesis of 2-imidazolines. This reaction proceeds via the coupling of imines, acid chlorides and carbon monoxide to form imidazolinium carboxylates, followed by a decarboxylation. Decarboxylation in CHCl3 is found to result in a mixture of imidazolinium and imidazolium salts. However, the addition of benzoic acid suppresses aromatization, and generates the trans-disubstituted imidazolines in good yield. Combining this reaction with subsequent nitrogen deprotection provides an overall synthesis of imidazolines from multiple available building blocks.
Keywords: 2-imidazoline; palladium; catalysis; multicomponent synthesis 2-imidazoline; palladium; catalysis; multicomponent synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Supplementary material

SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
MDPI and ACS Style

Xu, B.; Worrall, K.; Arndtsen, B.A. Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides. Molecules 2012, 17, 13759-13768.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert