K2CO3-Promoted Formal [3+3]-Cycloaddition of N-Unsubstituted Isatin N, N'-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

doi:10.3390/molecules28031034

K₂CO₃-Promoted Formal [3+3]-Cycloaddition of N-Unsubstituted Isatin N, N'-Cyclic Azomethine Imine 1,3-Dipoles with Knoevenagel Adducts

Molecules. 2023 Jan 19;28(3):1034. doi: 10.3390/molecules28031034.

Authors

Guosheng Yang¹, Sicheng Li², Qiumi Wang¹, Huabao Chen³, Chunping Yang³, Zhongqiong Yin⁴, Xu Song⁴, Li Zhang¹, Cuifen Lu⁵, Guizhou Yue¹

Affiliations

¹ College of Science, Sichuan Agricultural University, Ya'an 625014, China.
² The Yingjing County Emergency Management Agency, Ya'an 625200, China.
³ College of Agronomy, Sichuan Agricultural University, Chengdu 611130, China.
⁴ College of Veterinary Medicine, Sichuan Agricultural University, Chengdu 611130, China.
⁵ 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.

Abstract

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.

Keywords: Knoevenagel adduct; azomethine ylide; cycloaddition; spiropyridazine oxoindole; synthesis.

Abstract

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