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A green, multicomponent, regio- and stereo-selective 1,3-dipolar cycloaddition of azides and azomethine ylides generated in situ with bifunctional dipolarophiles using PEG-400

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Abstract

A series of novel dispiropyrrolidine-linked 1,2,3-triazole derivatives have been prepared by one-pot, four-component protocol that employed 5-arylidene-3-(prop-2-ynyl)thiazolidine-2,4-dione, isatin, sarcosine and substituted azides using Cu(I) generated in situ as catalyst in PEG-400 as a highly efficient and green media. This is the first report of a four-component reaction involving a classical Huisgen reaction, in which the two dipolar moieties (substituted azides and in situ generated azomethine ylides) react with acetylenic and olefinic dipolarophiles, respectively. The 1,3-dipolar cycloaddition proceeds in a highly regio- and stereo-selective manner. This methodology can be an ideal tool for the preparation of biologically important five-membered heterocyclic compounds in one pot.

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Acknowledgments

JS and HS thank UGC, New Delhi, India for the grant of Junior Research Fellowships.

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  1. Department of Chemistry, University of Delhi, Delhi, 110007, India

    Jayant Sindhu, Harjinder Singh & J. M. Khurana

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  1. Jayant Sindhu
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Correspondence to J. M. Khurana.

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Sindhu, J., Singh, H. & Khurana, J.M. A green, multicomponent, regio- and stereo-selective 1,3-dipolar cycloaddition of azides and azomethine ylides generated in situ with bifunctional dipolarophiles using PEG-400. Mol Divers 18, 345–355 (2014). https://doi.org/10.1007/s11030-014-9505-y

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