Journal
MOLECULES
Volume 28, Issue 3, Pages -Publisher
MDPI
DOI: 10.3390/molecules28031034
Keywords
azomethine ylide; cycloaddition; Knoevenagel adduct; spiropyridazine oxoindole; synthesis
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The synthesis of dicyclic spiropyridazine oxoindole derivatives by [3+3]-cycloaddition reaction of N-unsubstituted isatin N,N'-cyclic azomethine imine 1,3-dipoles was successfully achieved. The products, having two consecutive stereocenters including spiroquaternary stereocenters in one ring structure, were obtained in moderate to excellent yields (20-93%) and low to moderate diastereoselectivities (1:9-10:1 dr). The synthesized compounds were thoroughly characterized using various spectroscopic techniques.
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.
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