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

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

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 effe...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2023-01, Vol.28 (3), p.1034
Hauptverfasser: Yang, Guosheng, Li, Sicheng, Wang, Qiumi, Chen, Huabao, Yang, Chunping, Yin, Zhongqiong, Song, Xu, Zhang, Li, Lu, Cuifen, Yue, Guizhou
Format: Artikel
Sprache:eng
Schlagworte:
Adducts
azomethine ylide
Cycloaddition
Dipoles
Hydrocarbons
Knoevenagel adduct
NMR
Nuclear magnetic resonance
Potassium carbonate
Ring structures
Single crystals
Solvents
Spectral analysis
spiropyridazine oxoindole
synthesis
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Zusammenfassung: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28031034