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Synlett 2011(2): 245-248  
DOI: 10.1055/s-0030-1259308
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© Georg Thieme Verlag Stuttgart ˙ New York

Formation of 3-Aminofuran-2-(5H)-ones and 3-Amino-1H-pyrrole-2,5-diones by Rearrangement of Isoxazolidines

Daniela Iannazzo*a, Caterina Carnovalea, Salvatore V. Giofrèa, Roberta Ettaria, Giovanni Romeoa, Roberto Romeoa, Giuseppe Lanzab, Ugo Chiacchiob
a Dipartimento Farmaco-Chimico, Università di Messina, Viale SS. Annunziata, 98168 Messina, Italy
Fax: +39(090)6766562; e-Mail: diannazzo@unime.it;
b Dipartimento di Scienze Chimiche, Università di Catania, Viale Andrea Doria 6, 95125 Catania, Italy
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Publication History

Received 16 December 2010
Publication Date:
10 January 2011 (online)

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Abstract

A novel rearrangement pathway of 3-alkoxycarbonyl-4-carbamoylisoxazolidines, leading to 1H-pyrrole-2,5-diones by treatment with TBAF, is reported. DFT quantum chemical calculations support the reaction route, controlled by ring strain, which proceeds through the opening of a bicyclic intermediate, with aldehyde extrusion.

Key words

1,3-dipolar cycloaddition - isoxazolidines - furan-2(5H)-ones - 1H-pyrrole-2,5-diones - density function calculations

    References and Notes

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Quenching the reaction of 9a with TBAF at 30 min, we have observed by TLC analysis traces of 12a.