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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Crystallographic data for 2a and 3c have been deposited in the Cambridge Crystallographic Data Centre with the deposition numbers CCDC 1473724. Copies of these data can be obtained free of charge via www.ccdc.ca-m.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB21EZ, UK; fax: +44 1223 336033; or e-mail: deposit@ccdc.cam.ac.uk)
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The authors acknowledge the University of Tehran for financial support of this research.
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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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DOI: https://doi.org/10.1007/s13738-016-0886-y