Heterocyclizations at the Isocyanide Carbon: Mechanistic Insights into the 2-Isocyanoaniline to Benzimidazole Conversion
Abstract
High Resolution Image Download MS PowerPoint Slide Benzo-fused heteroazacycles can form through spontaneous cyclizations of phenylisocyanides bearing some electron donor substituents at the ortho position. Although such reactions have been known since the 1970s, a clear mechanistic understanding of these transformations remains absent. Here, we disclose a detailed computational analysis aimed at elucidating the more plausible mechanism for one of these cyclizations, the o -isocyanoaniline to benzimidazole conversion. Our results show that a transient 1,4-diazabutatriene could play a key role in this cyclization by enabling a reaction pathway of lower barrier than the unimolecular concerted process.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Synthesis and Reactivity of Heterocycles
Synthesis of heterocyclic compounds
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 4
- Pages
- 1837–1841
- Publication date
- 15 January 2026
- Language
- EN