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.
Highlights
This reaction proceeds via the coupling of imines, acid chlorides and carbon monoxide to form imidazolinium carboxylates, followed by a decarboxylation
We have previously reported a palladium-catalyzed multicomponent synthesis of imidazolinium carboxylates from imines, acid chlorides and CO (Scheme 1) [25,26,27]
In order to test the viability of this chemistry in imidazoline synthesis, imidazolinium carboxylate
Summary
2-Imidazolines, the 4,5-reduced counterpart of imidazoles, are an important class of small molecules. Other synthetic routes to imidazolines have been reported, including the ring opening of aziridines [19,20], the reaction of imines with isocyanates [21,22,23], and the cycloaddition of imines to Molecules 2012, 17 azomethine ylides [24]. While these methods are each effective, they often require the use of synthetic precursors which can themselves require a multistep synthesis.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
