Rapid abnormal [3+2]-cycloaddition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones

Guizhou Yue; Zhengjie Dou; Zexi Zhou; Li Zhang; Juhua Feng; Huabao Chen; Zhongqiong Yin; Xu Song; Xiaoxia Liang; Xianxiang Wang; Hanbing Rao; Cuifen Lu

doi:10.1039/D0NJ00887G

Rapid abnormal [3+2]-cycloaddition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones†

Guizhou Yue,

‡*^a Zhengjie Dou,‡^a Zexi Zhou,^a Li Zhang,^a Juhua Feng,

^a Huabao Chen,

^b Zhongqiong Yin,^c Xu Song,^c Xiaoxia Liang,^c Xianxiang Wang,

^a Hanbing Rao^a and Cuifen Lu*^d

Author affiliations

* Corresponding authors

^a College of Science, Sichuan Agricultural University, Ya’an, Sichuan, China
E-mail: yueguizhou@sicau.edu.cn

^b College of Agricultural Sciences, Sichuan Agricultural University, Chengdu, Sichuan, China

^c College of Veterinary Medicine, Sichuan Agricultural University, Chengdu, Sichuan, China

^d Hubei Collaborative Innovation Center for Advanced Organochemical Materials & Ministry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University, Wuhan 430062, China
E-mail: lucf@hubu.edu.cn

Abstract

The rapid synthesis of novel dicyclic spiropyrrolidine was reported, using [3+2]-cycloaddition of isatin N,N′-cyclic azomethine imine 1,3-dipoles, generated from the condensation of substituted isatins and pyrazolidones, with chalcones in 2–5 min. The dicyclic spiropyrrolidine oxoindole was smoothly acquired in moderate to excellent yields (35–95%) with high diastereoselectivities (>20 : 1 dr).

New Journal of Chemistry

Rapid abnormal [3+2]-cycloaddition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Rapid abnormal [3+2]-cycloaddition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones

Social activity

Search articles by author

Spotlight

Advertisements