The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic Insights.
Where this comes from
- Record sourced from PubMed, PMID 27224656.
- Also identified by DOI 10.1371/journal.pone.0156129 and PMC identifier 4880325.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
Abstract
New insights concerning the reaction mechanism in the cycloaddition reaction of benzimidazolium ylides to activated alkynes are presented. The proposed pathway leading both to 2-(1H-pyrrol-1-yl)anilines and to pyrrolo[1,2-a]quinoxalin-4(5H)-ones involves an opening of the imidazole ring from the cycloaddition product, followed by a nucleophilic attack of the aminic nitrogen to a proximal carbonyl group and the elimination of a leaving group. The mechanistic considerations are fully supported by experimental data, including the XRD resolved structure of the key reaction intermediate.
Medical subject headings
- Alkynes
- Aniline Compounds
- Quinoxalines