Synthesis of oxaprozin analogs from 2H-azirines and cyclic anhydrides
We report a novel, transition-metal- and base-free cascade reaction between 2H-azirines and cyclic anhydrides, yielding oxaprozin analogs containing a trisubstituted oxazole core through a ring-opening and annulation sequence. The method exhibits broad functional group tolerance, high bond-forming e...
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| Autori principali: | , , , , , , , |
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| Natura: | Article (Journal) |
| Lingua: | inglese |
| Pubblicazione: |
1 April 2026
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| In: |
Organic & biomolecular chemistry
Year: 2026, Volume: 24, Fascicolo: 13, Pages: 2761-2767 |
| ISSN: | 1477-0539 |
| DOI: | 10.1039/d6ob00168h |
| Accesso online: | Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1039/d6ob00168h Verlag, lizenzpflichtig, Volltext: https://pubs.rsc.org/ob/article/24/13/2761/1233850/Synthesis-of-oxaprozin-analogs-from-2H-azirines 
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| Note sull'autore: | Reyhaneh Azimi, Kamran Amiri, S. Sina Hosseini, Robert Stranger, Alireza Ariafard, Frank Rominger, Hamid Reza Bijanzadeh and Saeed Balalaie |
| Riassunto: | We report a novel, transition-metal- and base-free cascade reaction between 2H-azirines and cyclic anhydrides, yielding oxaprozin analogs containing a trisubstituted oxazole core through a ring-opening and annulation sequence. The method exhibits broad functional group tolerance, high bond-forming efficiency, and excellent atom economy, providing the desired products in good to excellent yields. Interestingly, we found that a small amount of dicarboxylic acid, formed adventitiously through partial hydrolysis of the anhydride, acts as a catalyst for this transformation. DFT calculations support the proposed mechanism and confirm the catalytic role of the dicarboxylic acid. This protocol offers a practical and efficient strategy for accessing oxaprozin-type frameworks from readily available starting materials. |
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| Descrizione del documento: | Online veröffentlicht am: 19. Februar 2026 Gesehen am 22.07.2026 |
| Descrizione fisica: | Online Resource |
| ISSN: | 1477-0539 |
| DOI: | 10.1039/d6ob00168h |