An Unexpected Formation of Spiro Isoxazoline-Dihydrofurane Compounds from Substituted Ketofurfuryl Alcohols
Oximation of substituted ketofurfuryl alcohols in the presence of hydroxylamine hydrochloride and pyridine in ethanol as solvent led to a new class of spiro derivatives presenting a 7-methylene-1,6-dioxa-2-azaspiro [4.4] nona-2,8-diene skeleton along with, in some cases, the predictable oxime. The structures of such spiro compounds were determined by 2D NMR spectroscopy. The suggested formation of this skeleton involves an in situ oximation/dehydration/S<sub>N</sub>' cascade reaction.
Authors
- Claire Cuyamendous (ORCID: https://orcid.org/0000-0003-3997-1229)
- Christine Saluzzo (ORCID: https://orcid.org/0000-0002-4055-5946)
- Mathieu Y. Laurent (ORCID: https://orcid.org/0000-0003-4904-2095)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Le Mans Université (FR)
- Institut des Molécules et Matériaux du Mans (FR)
Publication Details
- Journal
- Molecules
- Published
- 2024-11-20
- DOI
- https://doi.org/10.3390/molecules29225474
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Ministère de l'Enseignement Supérieur et de la Recherche
- Centre National de la Recherche Scientifique