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Eco-friendly synthesis of novel thiohydantoin-type sulfur-containing imidazolinone derivatives from glycine ester

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Chemistry of Heterocyclic Compounds Aims and scope

Imino derivatives of glycine ester were prepared from methyl glycinate by the known procedure and then they reacted with several amines under microwave irradiation without solvent that gave the corresponding glycine amides. By the one-component cyclocondensation, the obtained amide derivatives were transformed into thiohydantoin-type imidazolinones using solvent-free microwave procedure. All imine-ester derivatives and most of the imidazolinone derivatives were synthesized for the first time. This eco-friendly protocol can provide a suitable way for synthesizing new potentially bioactive imidazolinone derivatives.

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Notes

  1. In compounds 9a–h proton NH is exchangable by D2O heated at 85°C.

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The work was supported by Artvin Coruh University research project (BAP-2012.F19.02.24) and Hellenic Republic Ministry of Education, State Scholarships Foundation (I.K.Y.) of Greece (Grant No. 1211). We thank the NMR center at the University of Ioannina for the spectra.

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Authors and Affiliations

  1. Science-Technology Research and Application Center, Artvin Coruh University, Artvin, 08000, Turkey

    Mustafa Kemal Gümüş

  2. Department of Chemistry, University of Ioannina, Ioannina, 45110, Greece

    Mustafa Kemal Gümüş & Yiannis Elemes

Authors
  1. Mustafa Kemal Gümüş
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  2. Yiannis Elemes
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Corresponding author

Correspondence to Mustafa Kemal Gümüş.

Additional information

This work is dedicated to the memory of Professor Yiannis Elemes

Supplementary information file containing NMR spectral data of compounds 8b, 9a–d, 10a–d is available at the journal website at http://link.springer.com/journal/10593.

Yiannis Elemes is deceased.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(2), 153–157

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Gümüş, M.K., Elemes, Y. Eco-friendly synthesis of novel thiohydantoin-type sulfur-containing imidazolinone derivatives from glycine ester. Chem Heterocycl Comp 54, 153–157 (2018). https://doi.org/10.1007/s10593-018-2247-5

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  • DOI: https://doi.org/10.1007/s10593-018-2247-5

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