Direct C(sp 2 )-H Eliminative Nucleophilic Alkylation of 2 H ‐Imidazole N‐Oxides With Ketones Toward Imidazole‐Derived Enaminones

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Abstract
An efficient method based on the nucleophilic functionalization of nonaromatic 2 H ‐imidazole 1‐oxides with carbonyl compounds has been developed for the first time to afford a wide range of azaheterocyclic enaminonic compounds of various architectures in yields of up to quantitative. It has been found that the reaction proceeds via a nucleophilic hydrogen substitution (S N H AE) mechanism, in which sodium sulfide (Na 2 S) serves as a base, generating an active carbanion. The enaminone derivatives can be deprotonated to result in the promising dimeric molecular systems. The postmodification of enaminones containing a CBr bond has also been carried out via the Suzuki–Miyaura cross‐coupling reaction. The obtained compounds are of interest in the design of pharmacologically active compounds ligands and building blocks of functional materials.
Funding Information
  • Russian Science Foundation (23‐63‐10011)

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