Display options
Cite
Collet JW, Ackermans K, Lambregts J, et al. Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade. J Org Chem. 2018;83(2):854-861doi: 10.1021/acs.joc.7b02844.
Collet, J. W., Ackermans, K., Lambregts, J., Maes, B. U. W., Orru, R. V. A., & Ruijter, E. (2018). Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade. The Journal of organic chemistry, 83(2), 854-861. https://doi.org/10.1021/acs.joc.7b02844
Collet, Jurriën W, et al. "Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade." The Journal of organic chemistry vol. 83,2 (2018): 854-861. doi: https://doi.org/10.1021/acs.joc.7b02844
Collet JW, Ackermans K, Lambregts J, Maes BUW, Orru RVA, Ruijter E. Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade. J Org Chem. 2018 Jan 19;83(2):854-861. doi: 10.1021/acs.joc.7b02844. Epub 2018 Jan 02. PMID: 29260564; PMCID: PMC5778392.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 2018 Jan 19;83(2):854-861. doi: 10.1021/acs.joc.7b02844. Epub 2018 Jan 02.

Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade.

The Journal of organic chemistry

Jurriën W Collet, Kelly Ackermans, Jeffrey Lambregts, Bert U W Maes, Romano V A Orru, Eelco Ruijter

Affiliations

  1. Department of Chemistry and Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines & Systems (AIMMS), Vrije Universiteit Amsterdam , De Boelelaan 1108, 1081 HZ Amsterdam, The Netherlands.
  2. Organic Synthesis, Department of Chemistry, University of Antwerp , Groenenborgerlaan 171, 2020 Antwerp, Belgium.

PMID: 29260564 PMCID: PMC5778392 DOI: 10.1021/acs.joc.7b02844

Abstract

We developed a one-pot, two-stage synthetic route to substituted 4-aminoquinolines involving an imidoylative Sonogashira coupling followed by acid-mediated cyclization. This three-component reaction affords pharmaceutically valuable 4-aminoquinolines in a one-pot procedure from readily available starting materials. The reaction tolerates various substituents on the arene as well as the use of secondary and even primary isocyanides. Additionally, the wide tolerance for functionalized isocyanides allows for the one-pot synthesis of various substituted chloroquine analogues as well as other medicinally relevant products.

References

  1. Bioorg Med Chem Lett. 2012 Oct 15;22(20):6494-7 - PubMed
  2. Pharmacol Rev. 2016 Jan;68(1):142-67 - PubMed
  3. J Pharmacol Exp Ther. 1999 Dec;291(3):1337-47 - PubMed
  4. N Engl J Med. 2016 Jan 7;374(1):23-32 - PubMed
  5. PLoS One. 2013;8(4):e60579 - PubMed
  6. Bioorg Med Chem Lett. 2000 Jul 3;10(13):1409-12 - PubMed
  7. J Org Chem. 2013 Apr 5;78(7):3170-5 - PubMed
  8. J Med Chem. 2015 Oct 22;58(20):7991-8010 - PubMed
  9. Nat Med. 2013 Feb;19(2):156-67 - PubMed
  10. Angew Chem Int Ed Engl. 2016 Mar 7;55(11):3823-7 - PubMed
  11. Bioorg Med Chem Lett. 1999 Jul 5;9(13):1819-24 - PubMed
  12. Angew Chem Int Ed Engl. 2012 Dec 21;51(52):13058-61 - PubMed
  13. J Org Chem. 2015 Feb 6;80(3):1464-71 - PubMed
  14. Eur J Med Chem. 2004 Dec;39(12 ):1047-57 - PubMed
  15. Nature. 2010 May 20;465(7296):297-8 - PubMed
  16. J Org Chem. 2015 Jun 5;80(11):5764-70 - PubMed
  17. Bioorg Med Chem. 2015 Feb 15;23(4):742-52 - PubMed
  18. Nature. 2002 Feb 7;415(6872):686-93 - PubMed
  19. Org Biomol Chem. 2016 Aug 7;14 (29):7053-60 - PubMed
  20. Org Biomol Chem. 2013 Nov 14;11(42):7267-70 - PubMed
  21. J Med Chem. 1994 Apr 15;37(8):1126-35 - PubMed
  22. J Med Chem. 2014 Jul 24;57(14):6240-51 - PubMed
  23. J Org Chem. 2005 Aug 5;70(16):6454-60 - PubMed
  24. J Med Chem. 2003 Mar 27;46(7):1242-9 - PubMed
  25. J Med Chem. 2000 Nov 30;43(24):4667-77 - PubMed
  26. Bioorg Med Chem Lett. 2005 Feb 15;15(4):1015-8 - PubMed
  27. Chem Biol Interact. 1982 Nov;42(2):153-64 - PubMed
  28. Nature. 1992 Jan 9;355(6356):108-9 - PubMed
  29. J Immunol. 2011 Apr 15;186(8):4794-804 - PubMed
  30. Org Lett. 2017 Aug 4;19(15):3994-3997 - PubMed
  31. Pharmacol Rev. 2005 Mar;57(1):117-45 - PubMed
  32. Org Biomol Chem. 2004 Jul 21;2(14):1974-6 - PubMed

Publication Types