Synthesis of Benzimidazol-2-ones by Oxidative Cyclization Ring Closure of Amido-Urea Precursors
We describe herein the synthesis of novel benzimidazol-2-ones by oxidative cyclization of amido-urea precursors, using bis(acetoxy)iodobenzene. The role of the oxidative reagent and the formation of the benzimidazol-2-one products were demonstrated and supported by X-ray diffraction. Optimization of the reaction conditions was performed, and the generality of the reaction was shown. The reaction scope was found to be limited to amino-urea substrates bearing a C(sp<sup>3</sup>) atom adjacent to the amide carbonyl group. A mechanistic pathway involving a Hofmann rearrangement was proposed.
Authors
- Augustin M. Mădălan (ORCID: https://orcid.org/0000-0002-2275-5004)
- Codruța C. Popescu (ORCID: https://orcid.org/0000-0003-2341-5367)
- Cătălin C. Anghel (ORCID: https://orcid.org/0000-0001-5540-4158)
- Maria‐Cristina Popescu (ORCID: https://orcid.org/0000-0003-4543-2870)
- Cristian Dobrotǎ
- Anamaria Hanganu (ORCID: https://orcid.org/0000-0002-0433-752X)
- Mihaela Matache (ORCID: https://orcid.org/0000-0001-7956-7162)
- Anca Păun
Institutions
- University of Bucharest (RO)
- Babeș-Bolyai University (RO)
- Department of Physics, Mathematics and Informatics (BY)
- Toronto and Region Conservation Authority (CA)
- Romanian Academy (RO)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-10-27
- DOI
- https://doi.org/10.1021/acs.joc.5c01551
- Primary Topic
- Synthesis of heterocyclic compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00