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

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.

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.

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