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

Autoren

  • 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
Weitere Informationen

Publikationsverlauf

Received: 23. September 2015

Accepted after revision: 27. Oktober 2015

Publikationsdatum:
25. November 2015 (online)


Graphical Abstract

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