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Diastereoselective synthesis of novel N-substituted pyrrolidine-2-one containing piperazine derivatives

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Abstract

Synthesis of novel hybrid derivatives of two known scaffolds, pyrrolidine-2-one and piperazine, is described. Initially, the Ugi reaction of phenylglyoxal, aromatic amines, coumarin-3-carboxylic acid and isocyanides in methanol resulted in the formation of dihydrochromeno[3,4-c]pyrrole-3,4-diones. The obtained products were then treated with N-alkylpiperazines in dichloromethane to afford the novel N-substituted pyrrolidine-2-one containing piperazine derivatives in satisfactory yields. The proof of the structures was carried out by means of spectroscopic information and X-ray crystallography.

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Acknowledgments

The authors acknowledge the University of Tehran for financial support of this research.

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Authors and Affiliations

  1. School of Chemistry, College of Science, University of Tehran, Tehran, P.O. Box 14155, 6455, Iran

    Mehdi Ghandi, Meysam Khodadadi & Alireza Abbasi

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  1. Mehdi Ghandi
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  2. Meysam Khodadadi
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  3. Alireza Abbasi
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Correspondence to Mehdi Ghandi.

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Ghandi, M., Khodadadi, M. & Abbasi, A. Diastereoselective synthesis of novel N-substituted pyrrolidine-2-one containing piperazine derivatives. J IRAN CHEM SOC 13, 1691–1698 (2016). https://doi.org/10.1007/s13738-016-0886-y

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