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Trimesic acid is a suitable building block in triple four-component Ugi reaction: access to unique trivalent compounds

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Abstract

A triple four-component Ugi reaction of isocyanide, amine, aldehyde, and trimesic acid as the acid component with three acidic functional groups in MeOH at 65 °C has been disclosed. The process employs readily available and low-cost reagents, a convenient synthetic procedure, and mild reaction conditions for the synthesis of pharmacologically significant and structurally interesting compounds with several peptide groups, suitable for dendrimers and self-assembling. Substituents could be independently varied at three different positions. The structural assignments are supported by 1H and 13C NMR data.

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References

  1. Herrera RP, Marques-Lopez E (2015) Multicomponent reactions: Concepts and applications for design and synthesis. Wiley-VCH, Weinheim

    Google Scholar 

  2. Mohammadi A, Taheri S, Amini A, Ahdenov R (2018) Mol Divers 22:999

    Article  CAS  Google Scholar 

  3. Nenajdenko VG (2012) Isocyanide chemistry: Applications in synthesis and material science. Wiley-VCH, Weinheim

    Book  Google Scholar 

  4. Berkel SSV, Bögels BGM, Wijdeven MA, Westermann B, Rutjes FPGT (2012) Eur J Org Chem 2012:3543

    Article  Google Scholar 

  5. Afshari R, Shaabani A (2018) ACS Comb Sci 20:499

    Article  CAS  Google Scholar 

  6. Koopmanschap G, Ruijter E, Orru RVA (2014) Beilstein J Org Chem 10:544

    Article  Google Scholar 

  7. Dömling A, Wang W, Wang K (2012) Chem Rev 112:3083

    Article  Google Scholar 

  8. Ghashghaei O, Seghetti F, Lavilla R (2019) Beilstein J Org Chem 15:521

    Article  CAS  Google Scholar 

  9. Wessjohann LA, Filho RAW, Rivera DG (2012) Multiple multicomponent reactions with isocyanides. In: Nenajdenko VG (ed) Isocyanide chemistry. Wiley-VCH, Weinheim, p 233

    Chapter  Google Scholar 

  10. Ghashghaei O, Caputo S, Sintes M, Reves M, Kielland N, Estarellas C, Luque FJ, Avino A, Eritja R, Serna-Gallego A, Marrugal-Lorenzo JA, Pachon J, Sanchez-Cespedes J, Treadwell R, Moliner F, Vendrell M, Lavilla R (2018) Chem Eur J 24:1

    Article  Google Scholar 

  11. Shaabani A, Ghadari R, Sarvary A, Rezayan A (2009) J Org Chem 74:4372

    Article  CAS  Google Scholar 

  12. Echemendía R, Rabêlo WF, López ER, Coro J, Suárez M, Paixão MW, Rivera DG (2018) Tetrahedron Lett 59:5040

    Article  Google Scholar 

  13. Balalaie S, Bigdeli M, Sheikhhosseini E, Habibi A, Piri Moghadam H, Naderi M (2012) Helv Chim Acta 95:528

    Article  CAS  Google Scholar 

  14. Halimehjani AZ, Habibi A, Hassannezhad A (2015) Org Chem Indian J 11:70

    CAS  Google Scholar 

  15. Aknin K, Gauriot M, Totobenazara J, Deguine N, Deprez-Poulain R, Deprez B, Charton J (2012) Tetrahedron Lett 53:458

    Article  CAS  Google Scholar 

  16. Llevot A, Boukis AC, Oelmann S, Wetzel K, Meier MAR (2017) Top Curr Chem 375:66

    Article  Google Scholar 

  17. Kreye O, Turunc O, Sehlinger A, Rackwitz J, Meier MAR (2012) Chem Eur J 18:5767

    Article  CAS  Google Scholar 

  18. Shaabani A, Sarvary A, Shaabani S (2014) With isocyanide participation. In: Muller TJJ (ed) Multicomponent reactions 2. Thieme, Stuttgart, p 55

    Google Scholar 

  19. Maleki A, Sarvary A (2015) RSC Adv 5:60938

    Article  CAS  Google Scholar 

  20. Sarvary A, Maleki A (2015) Mol Divers 19:189

    Article  CAS  Google Scholar 

  21. Sarvary A, Shaabani S, Ghanji N, Shaabani A (2015) J Sulfur Chem 36:117

    Article  CAS  Google Scholar 

  22. Ramezanpour S, Panahi A, Rominger F (2018) Monatsh Chem 149:625

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge financial support from the Research Council of Shahrood University of Technology and Babol Noshirvani University of Technology.

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Correspondence to Hossein Nasr-Isfahani or Afshin Sarvary.

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Dehghan, N., Nasr-Isfahani, H., Sarvary, A. et al. Trimesic acid is a suitable building block in triple four-component Ugi reaction: access to unique trivalent compounds. Monatsh Chem 151, 397–404 (2020). https://doi.org/10.1007/s00706-020-02554-0

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  • DOI: https://doi.org/10.1007/s00706-020-02554-0

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