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Diastereoselective synthesis of peptidomimetics in one-pot Ugi reaction using trans-4-isopropylcyclohexanecarboxylic acid

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Abstract

The use of trans-4-isopropylcyclohexanecarboxylic acid as a substitution for the carboxylic acid component in the Ugi multicomponent condensation that leads to (1R,4R)-N-(2-(cyclohexylamino)-2-oxo-4-isopropylcyclohexane-1-carboxamide derivatives is described for the first time. One pot, clean reaction, and excellent yields are some advantages of this protocol.

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References

  1. Ugi I, Werner B, Dömling A (2003) Molecules 8:53

    Article  CAS  Google Scholar 

  2. Dömling A, Ugi I (2000) Angew Chem Int Ed 39:3168

    Article  Google Scholar 

  3. Ugi I, Dömling A, Horl W (1994) Endeavour 18:115

    Article  CAS  Google Scholar 

  4. Dömling A (2002) Curr Opin Chem Biol 6:306

    Article  Google Scholar 

  5. Hulme C, Gore V (2003) Curr Med Chem 10:51

    Article  CAS  Google Scholar 

  6. Dömling A (2006) Chem Rev 106:17

    Article  Google Scholar 

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

    Article  Google Scholar 

  8. Zarganes-Tzitzikas T, Chandgude AL, Dömling A (2015) Chem Rec 15:981

    Article  CAS  Google Scholar 

  9. Ugi I, Meyr R, Fetzer U, Steinbruckner C (1959) Angew Chem 71:386

    Google Scholar 

  10. Ruijter E, Scheffelaar R, Orru RV (2011) Angew Chem Int Ed 50:6234

    Article  CAS  Google Scholar 

  11. Burke MD, Schreiber SL (2004) Angew Chem Int Ed 43:46

    Article  Google Scholar 

  12. Tan DS (2005) Nat Chem Biol 1:74

    Article  CAS  Google Scholar 

  13. Nören-Müller A, Reis-Corréa JI, Prinz H, Rosenbaum C, Saxena K, Schwalbe HJ, Vestweber D, Cagna G, Schunk S, Schwarz O, Schiewe H, Waldmann H (2006) Proc Natl Acad Sci USA 103:10606

    Article  Google Scholar 

  14. Aravind A, Kumar PS, Sankar MG, Baskaran S (2011) Eur J Org Chem 2011:6980

    Article  CAS  Google Scholar 

  15. Orru RVA, Ruijter E (2010) Synthesis of heterocycles via multicomponent reactions II. Springer, Heidelberg

    Google Scholar 

  16. Gulevich AV, Zhdanko AG, Orru RVA (2010) Chem Rev 110:5235

    Article  CAS  Google Scholar 

  17. Gulevich AV, Balenkova ES, Nenajdenko VG (2007) J Org Chem 72:7878

    Article  CAS  Google Scholar 

  18. Jida M, Betti C, Lipkowska ZU, Tourwe D, Ballet S (2013) Org Lett 15:5866

    Article  CAS  Google Scholar 

  19. Zarezin DP, Khrustalev VN, Nenajdenko VG (2017) J Org Chem 82:6100

    Article  CAS  Google Scholar 

  20. Kriis K, Ausmees K, Pehk T, Lopp M, Kanger T (2010) Org Lett 12:2230

    Article  CAS  Google Scholar 

  21. Moni L, Banfi L, Basso A, Martino E, Riva R (2016) Org Lett 18:1638

    Article  CAS  Google Scholar 

  22. Pertejo P, Corres N, Torroba T, Valverde MG (2015) Org Lett 17:612

    Article  CAS  Google Scholar 

  23. Zhu C, Zuo Y, Wang R, Liang B, Yue X, Wen G, Shang N, Huang L, Chen Y, Du J, Bu X (2014) J Med Chem 57:6364

    Article  CAS  Google Scholar 

  24. Rice A, Liu Y, Michaelis ML, Himes RH, Georg GI, Audus KL (2005) J Med Chem 48:832

    Article  CAS  Google Scholar 

  25. Rao SN, Babu KS (2011) Org Commun 4:105

    CAS  Google Scholar 

  26. Liang G, Choi-Sledeski YM, Poli GB, Chen X, Minnich A, Wang Q, Tsay J, Sides K, Vaz R (2011) J Med Chem Commun 2:794

    Article  CAS  Google Scholar 

  27. Saito Y, Itagaki S, Otsuka Y, Kobayashi Y, Okumura H, Kobayashi M, Hirano T, Iseki K (2005) J Agric Food Chem 53:6100

    Article  CAS  Google Scholar 

  28. Soltesza ZI, Wanecqa E, Lombac A, Portillo MP, Pellati F, Szoko E, Bour S, Woodley F, Milagroc FI, Martinezc JA, Valeta P, Carpenea C (2010) Pharmacol Res 61:355

    Article  Google Scholar 

  29. Ramezanpour S, Balalaie S, Rominger F (2016) Tetrahedron 72:6409

    Article  CAS  Google Scholar 

  30. Ramezanpour S, Balalaie S, Rominger F, Bijanzadeh HR (2013) Tetrahedron 69:3480

    Article  CAS  Google Scholar 

  31. Nikbakht A, Ramezanpour S, Balalaie S, Rominger F (2015) Tetrahedron 71:6790

    Article  CAS  Google Scholar 

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Acknowledgements

This research was supported by Grants from the Iran National Science Foundation (INSF).

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Correspondence to Sorour Ramezanpour.

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Ramezanpour, S., Panahi, A. & Rominger, F. Diastereoselective synthesis of peptidomimetics in one-pot Ugi reaction using trans-4-isopropylcyclohexanecarboxylic acid. Monatsh Chem 149, 625–633 (2018). https://doi.org/10.1007/s00706-017-2086-6

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  • DOI: https://doi.org/10.1007/s00706-017-2086-6

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