Display options
Share it on

Tetrahedron Lett. 2018 Oct 17;59(42):3801-3805. doi: 10.1016/j.tetlet.2018.09.014. Epub 2018 Sep 07.

Bismuth-Catalyzed Synthesis of 2-Substituted Quinazolinones.

Tetrahedron letters

Sandeep R Vemula, Dinesh Kumar, Gregory R Cook

Affiliations

  1. Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND 58108-6050, USA.
  2. Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER) - Ahmedabad, Gandhinagar 382355, Gujarat, India.

PMID: 31274936 PMCID: PMC6605782 DOI: 10.1016/j.tetlet.2018.09.014

Abstract

The bismuth-catalyzed oxidative condensation of aldehydes with 2-aminobenzamide under aerobic conditions is reported using ethanol as the solvent. Good to excellent isolated yields (68-95%) of the corresponding 2-substituted quinazolinones were obtained under mild reaction conditions with excellent functional group tolerance. The quinazolinones were further functionalized to afford

Keywords: Bismuth; Catalysis; Condensation; Green chemistry; Quinazolinone

References

  1. J Med Chem. 1999 Aug 12;42(16):3163-6 - PubMed
  2. J Med Chem. 2000 May 18;43(10):2019-30 - PubMed
  3. J Am Chem Soc. 2003 Nov 12;125(45):13628-9 - PubMed
  4. Org Lett. 2007 Mar 29;9(7):1311-4 - PubMed
  5. Nature. 2007 Dec 6;450(7171):810-2 - PubMed
  6. J Med Chem. 1991 Apr;34(4):1492-503 - PubMed
  7. Chem Commun (Camb). 2008 Dec 21;(47):6333-5 - PubMed
  8. Angew Chem Int Ed Engl. 2009;48(2):348-51 - PubMed
  9. Tetrahedron Lett. 2008;49(24):3888-3890 - PubMed
  10. Org Lett. 2011 Mar 18;13(6):1274-7 - PubMed
  11. J Org Chem. 2011 May 20;76(10):3846-52 - PubMed
  12. Chem Soc Rev. 2011 Sep;40(9):4649-707 - PubMed
  13. J Org Chem. 2011 Oct 7;76(19):7730-6 - PubMed
  14. Org Biomol Chem. 2012 Jan 14;10(2):240-3 - PubMed
  15. J Org Chem. 2012 Aug 17;77(16):7046-51 - PubMed
  16. J Med Chem. 1990 Jan;33(1):161-6 - PubMed
  17. Org Biomol Chem. 2013 May 7;11(17):2740-55 - PubMed
  18. Nat Chem. 2013 May;5(5):369-75 - PubMed
  19. Chemistry. 2013 Sep 16;19(38):12635-8 - PubMed
  20. J Med Chem. 1986 Nov;29(11):2403-9 - PubMed
  21. Org Biomol Chem. 2014 Feb 7;12(5):758-64 - PubMed
  22. Org Biomol Chem. 2014 Jun 21;12(23):3802-7 - PubMed
  23. J Org Chem. 2014 Jun 6;79(11):5082-7 - PubMed
  24. J Am Chem Soc. 2015 Feb 11;137(5):1738-41 - PubMed
  25. J Org Chem. 2015 Jul 2;80(13):6915-21 - PubMed
  26. J Med Chem. 2015 Aug 27;58(16):6678-96 - PubMed
  27. Acc Chem Res. 2016 Oct 4;49(10):2169-2178 - PubMed
  28. J Org Chem. 2017 Jul 21;82(14):7165-7175 - PubMed
  29. Bioorg Med Chem Lett. 1998 Mar 3;8(5):483-6 - PubMed

Publication Types

Grant support