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Amino Acids

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Ensembling three multicomponent reactions for the synthesis of a novel category of pseudo-peptides containing dithiocarbamate and N,X-heterocylic groups

  • Maryam Khalesi
  • Azim Ziyaei Halimehjani
  • Max Franz
  • Marc Schmidtmann
  • Jürgen Martens
Original Article

Abstract

Consecutive multicomponent reactions have been applied for the synthesis of novel pseudo-peptides bearing dithiocarbamate and N,X-heterocyclic groups (X = S, O) in only one structure. The first multicomponent reaction includes the synthesis of dithiocarbamates using an amine or amino acid, CS2 and an electrophile. The second MCR is synthesis of Asinger imines using 2-chloroisobutyraldehyde, NaXH (X = S, O), ketone and ammonia. The final MCR is Ugi reaction to afford the corresponding three-dimensional pseudo-peptides. Various Asinger imines, carboxylic acids and isocyanides were applied in this protocol to provide diversities of pseudo-peptides in high to excellent yields.

Keywords

Consecutive multicomponent reaction Pseudo-peptide Dithiocarbamate Asinger imine Ugi reaction 

Notes

Acknowledgements

We are grateful to the Iran National Science Foundation: INSF, Grant number 95829698, for supporting this work. We also thank the research council of Kharazmi University (Grant number D/2056) for supporting this work. We are thankful to the central analytic section of the University of Oldenburg for retrieving NMR and MS data.

Author contributions

Conceived and designed the experiments: AZH; JM. Performed the experiments and analyzed the data: MK; MF. X-ray data: MS. Wrote the paper: AZH; JM; MK; MF.

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.

Ethical standard

This article does not contain any studies with human participants or animals performed by any of the authors.

Informed consent

Informed consent was obtained from all individual participants included in the study.

Supplementary material

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Supplementary material 1 (PDF 1801 kb)
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Supplementary material 2 (PDF 5421 kb)
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Supplementary material 3 (PDF 708 kb)
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Supplementary material 4 (PDF 2317 kb)
726_2018_2661_MOESM5_ESM.docx (559 kb)
Supplementary material 5 (DOCX 559 kb)

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Organic Chemistry, Faculty of ChemistryKharazmi UniversityTehranIran
  2. 2.Institut für Chemie (IfC), Carl von Ossietzky Universität OldenburgOldenburgGermany

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