A Noncarbenoid Approach to Imidazolidines via ZnCl<sub>2</sub>-Catalyzed Annulation of 4-Alkoxycarbonyl-1,2-diaza-1,3-dienes with 1,3,5-Triazinanes
An unprecedented ZnCl<sub>2</sub>-catalyzed formal [2 + 2 + 1] annulation of 1,2-diaza-1,3-dienes (DDs) with hexahydro-1,3,5-triazines (HTs) has been accomplished, which provides imidazolidine frameworks with quaternary carbon centers. Thus, a new opportunity bypassing the use of hazardous diazo reagents is made possible by a unique carbene-like reactivity (C1 synthon) of readily available and safe 4-alkoxycarbonyl-1,2-diaza-1,3-butadienes. Besides, this noncarbenoid transformation can be implemented into a two-step three-component approach by utilizing the aromatic amine, 1,2-diaza-1,3-dienes and 1,3,5-triazines to synthesize differently substituted 1,3-diaryl imidazolidines.
Authors
- Sara Caselli
- Gianfranco Favi (ORCID: https://orcid.org/0000-0003-3112-819X)
- Giacomo Mari (ORCID: https://orcid.org/0000-0002-5076-942X)
- Fabio Mantellini (ORCID: https://orcid.org/0000-0002-1140-5404)
- Vittorio Ciccone (ORCID: https://orcid.org/0000-0002-7329-245X)
Institutions
- University of Urbino (IT)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-08-29
- DOI
- https://doi.org/10.1021/acs.joc.5c01387
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- European Commission
- Ministero dell'Università e della Ricerca