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 aldhehyde extrusion.
Formation of 3-Aminofuran-2-(5H)-ones and 3-Amino-1H-pyrrole-2,5-diones by Rearrangement of Isoxazolidines
IANNAZZO, Daniela;CARNOVALE, CATERINA;GIOFRE', Salvatore Vincenzo;ETTARI, Roberta;ROMEO, Giovanni;ROMEO, Roberto;
2011-01-01
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 aldhehyde extrusion.File in questo prodotto:
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