K<sub>2</sub>CO<sub>3</sub>-Promoted Formal [3+3]-Cycloaddition of <i>N</i>-Unsubstituted Isatin <i>N</i>,<i>N′</i>-Cyclic Azomethine Imine 1,3-Dipoles with Knoevenagel Adducts
Guosheng Yang,
Sicheng Li,
Qiumi Wang,
Huabao Chen,
Chunping Yang,
Zhongqiong Yin,
Xu Song,
Li Zhang,
Cuifen Lu,
Guizhou Yue
Affiliations
Guosheng Yang
College of Science, Sichuan Agricultural University, Ya’an 625014, China
Sicheng Li
The Yingjing County Emergency Management Agency, Ya’an 625200, China
Qiumi Wang
College of Science, Sichuan Agricultural University, Ya’an 625014, China
Huabao Chen
College of Agronomy, Sichuan Agricultural University, Chengdu 611130, China
Chunping Yang
College of Agronomy, Sichuan Agricultural University, Chengdu 611130, China
Zhongqiong Yin
College of Veterinary Medicine, Sichuan Agricultural University, Chengdu 611130, China
Xu Song
College of Veterinary Medicine, Sichuan Agricultural University, Chengdu 611130, China
Li Zhang
College of Science, Sichuan Agricultural University, Ya’an 625014, China
Cuifen Lu
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
Guizhou Yue
College of Science, Sichuan Agricultural University, Ya’an 625014, China
The synthesis of dicyclic spiropyridazine oxoindole derivatives by using [3+3]-cycloaddition of N-unsubstituted isatin N,N′-cyclic azomethine imine 1,3-dipoles was reported. The products bearing two consecutive stereocenters, including spiroquaternary stereocenters in one ring structure, can be effectively obtained in moderate to excellent yields (20–93%) and low to moderate diastereoselectivities (1:9–10:1 dr). The synthesized compounds (>35 examples) were characterized by single-crystal XRD, FTIR, NMR, and mass spectral analysis.
