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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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Detalles Bibliográficos
Autores principales: Azimi, Reyhaneh (Autor) , Amiri, Kamran (Autor) , Hosseini, S. Sina (Autor) , Stranger, Robert (Autor) , Ariafard, Alireza (Autor) , Rominger, Frank (Autor) , Bijanzadeh, Hamid Reza (Autor) , Balalaie, Saeed (Autor)
Formato: Article (Journal)
Lenguaje:inglés
Publicado: 1 April 2026
In: Organic & biomolecular chemistry
Year: 2026, Volumen: 24, Número: 13, Pages: 2761-2767
ISSN:1477-0539
DOI:10.1039/d6ob00168h
Acceso en línea: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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Notas de Autor:Reyhaneh Azimi, Kamran Amiri, S. Sina Hosseini, Robert Stranger, Alireza Ariafard, Frank Rominger, Hamid Reza Bijanzadeh and Saeed Balalaie
Descripción
Sumario: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.
Notas:Online veröffentlicht am: 19. Februar 2026
Gesehen am 22.07.2026
Descripción Física:Online Resource
ISSN:1477-0539
DOI:10.1039/d6ob00168h

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