Synthesis 2016; 48(04): 595-605
DOI: 10.1055/s-0035-1560966
paper
© Georg Thieme Verlag Stuttgart · New York

Diversity-Oriented Synthesis of Spiropyrazolone-Based Tetrahydropyrroles via Three-Component 1,3-Dipolar Cycloadditions

Qiong Wu*
a  School of Chemical Engineering and Technology, Key Laboratory of Coal Processing and Efficient Utilization of Ministry of Education, China University of Mining and Technology, Xuzhou 221111, P. R. of China
b  School of Chemistry and Chemical Engineering, Xuzhou Institute of Technology, Xuzhou 221111, P. R. of China   Email: hgwuqiong@xzit.edu.cn   Email: caipj@163.com
,
Chun Ma
b  School of Chemistry and Chemical Engineering, Xuzhou Institute of Technology, Xuzhou 221111, P. R. of China   Email: hgwuqiong@xzit.edu.cn   Email: caipj@163.com
,
Xi-Hua Du
b  School of Chemistry and Chemical Engineering, Xuzhou Institute of Technology, Xuzhou 221111, P. R. of China   Email: hgwuqiong@xzit.edu.cn   Email: caipj@163.com
,
Yan Chen
b  School of Chemistry and Chemical Engineering, Xuzhou Institute of Technology, Xuzhou 221111, P. R. of China   Email: hgwuqiong@xzit.edu.cn   Email: caipj@163.com
,
Pei-Jun Cai*
a  School of Chemical Engineering and Technology, Key Laboratory of Coal Processing and Efficient Utilization of Ministry of Education, China University of Mining and Technology, Xuzhou 221111, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 23 September 2015

Accepted after revision: 27 October 2015

Publication Date:
25 November 2015 (online)


Abstract

A highly efficient method for the synthesis of spiropyrazolone derivatives with structural diversity has been established via a facile three-component 1,3-dipolar cycloaddition of aldehydes, amino ester, and unsaturated pyrazolones. This protocol is applicable to a variety of unsaturated pyrazolones and aldehyde-derived azomethine ylides, providing an easy access to spiropyrazolone-based tetrahydro­pyrroles with structural diversity in high yields (up to 97%).

Supporting Information

 
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