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

Chuan-Chuan Wang; Jing Zhou; Zhi-Wei Ma; Xiao-Pei Chen; Ya-Jing Chen

doi:10.1039/C9OB01992H

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Synthesis of spirobarbiturate-pyrrolidinones via a domino aza-Michael/S_N2 cyclization of barbiturate-derived alkenes with N-alkoxy α-haloamides†

Chuan-Chuan Wang,

‡^ab Jing Zhou,‡^c Zhi-Wei Ma,^a Xiao-Pei Chen^a and Ya-Jing Chen

*^c

Author affiliations

* Corresponding authors

^a Faculty of Science, Henan University of Animal Husbandry and Economy, No. 2 Yingcai Street, Huiji District, Zhengzhou 450044, Henan, PR China

^b College of Chemistry, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, Henan, PR China

^c School of Pharmaceutical Sciences, Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education of China, Co-innovation Center of Henan Province for New Drug R & D and Preclinical Safety, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, Henan, PR China
E-mail: chenyj@zzu.edu.cn

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 S_N2 sequence, providing a practical tool in the synthesis of bioactive molecules spirobarbiturate-3-pyrrolidinones.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB01992H
Article type: Paper
Submitted: 11 Sep 2019
Accepted: 02 Oct 2019
First published: 02 Oct 2019

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Org. Biomol. Chem., 2019,17, 9200-9208

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Synthesis of spirobarbiturate-pyrrolidinones via a domino aza-Michael/S_N2 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, 17, 9200 DOI: 10.1039/C9OB01992H

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Organic & Biomolecular Chemistry