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Issue 7, 2018
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Solvent incorporated sequential [3 + 2] annulation/substitution reaction of azomethine imines and propargyl sulfur ylide

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Abstract

A novel solvent incorporated sequential [3 + 2] cycloaddition/substitution reaction of azomethine imines with propargyl sulfur ylide was developed. In the actual three-component reaction, propargyl sulfur ylide acts as a dipole reagent to furnish the annulation with azomethine imines, followed by the protic solvents acting as nucleophiles. The simple, mild, catalyst-free and practical protocol allows for the formation of N,N-bicyclic pyrazolidinones in moderate to excellent yields. Further transformation and gram-scale operations could also be achieved efficiently.

Graphical abstract: Solvent incorporated sequential [3 + 2] annulation/substitution reaction of azomethine imines and propargyl sulfur ylide

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Publication details

The article was received on 05 Dec 2017, accepted on 11 Jan 2018 and first published on 11 Jan 2018


Article type: Communication
DOI: 10.1039/C7OB03012F
Citation: Org. Biomol. Chem., 2018,16, 1068-1072
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    Solvent incorporated sequential [3 + 2] annulation/substitution reaction of azomethine imines and propargyl sulfur ylide

    S. Shen, Y. Yang, J. Duan, Z. Jia and J. Liang, Org. Biomol. Chem., 2018, 16, 1068
    DOI: 10.1039/C7OB03012F

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