DABCO-Catalyzed Mono-/Diallylation of <i>N</i>-Unsubstituted Isatin <i>N</i>,<i>N</i>′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates
Qiumi Wang,
Sicheng Li,
Guosheng Yang,
Xinyu Zou,
Xi Yin,
Juhua Feng,
Huabao Chen,
Chunping Yang,
Li Zhang,
Cuifen Lu,
Guizhou Yue
Affiliations
Qiumi Wang
College of Science, Sichuan Agricultural University, Ya’an 625014, China
Sicheng Li
The Yingjing County Emergency Management Agency, Ya’an 625200, China
Guosheng Yang
College of Science, Sichuan Agricultural University, Ya’an 625014, China
Xinyu Zou
College of Science, Sichuan Agricultural University, Ya’an 625014, China
Xi Yin
College of Science, Sichuan Agricultural University, Ya’an 625014, China
Juhua Feng
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
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
Allylation of N-unsubstituted isatin N,N′-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1–10 mol% DABCO in DCM at room temperature, rapidly gave N-allylated and N, β-diallylated isatin N,N′-cyclic azomethine imine 1,3-dipoles in moderate to high yields. The reaction features mild reaction conditions, easily practical operation, and short reaction times in most cases. Furthermore, the alkylated products were transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through the [3+2] or [3+3]-cycloaddition with maleimides or Knoevenagel adducts.
