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Synthesis of spirobarbiturate-pyrrolidinones via a domino aza-Michael/SN2 cyclization of barbiturate-derived alkenes with N-alkoxy α-haloamides

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Abstract

A highly efficient domino aza-MIRC (Michael Induced Ring Closure) reaction between barbiturate-derived alkenes and N-alkoxy α-haloamides has been achieved in moderate to excellent yields. This reaction proceeds smoothly under mild conditions via a domino aza-Michael addition/intramolecular SN2 sequence, providing a practical tool in the synthesis of bioactive molecules spirobarbiturate-3-pyrrolidinones.

Graphical abstract: Synthesis of spirobarbiturate-pyrrolidinones via a domino aza-Michael/SN2 cyclization of barbiturate-derived alkenes with N-alkoxy α-haloamides

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Publication details

The article was received on 11 Sep 2019, accepted on 02 Oct 2019 and first published on 02 Oct 2019


Article type: Paper
DOI: 10.1039/C9OB01992H
Org. Biomol. Chem., 2019, Advance Article

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    Synthesis of spirobarbiturate-pyrrolidinones via a domino aza-Michael/SN2 cyclization of barbiturate-derived alkenes with N-alkoxy α-haloamides

    C. Wang, J. Zhou, Z. Ma, X. Chen and Y. Chen, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01992H

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