The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic InsightsReport as inadecuate




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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-ylanilines and to pyrrolo1,2-aquinoxalin-45H-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.



Author: Costel Moldoveanu, Gheorghita Zbancioc , Dorina Mantu, Dan Maftei, Ionel Mangalagiu

Source: http://plos.srce.hr/



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