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Transition metal-free synthesis of quinolino[2′,3′:3,4]pyrazolo[5,1-b]quinazolin-8(6H)-ones via cascade dehydrogenation and intramolecular N-arylation

Abstract

2-(2-Chloroquinolin-3-yl)-3-(arylamino)-2,3-dihydroquinazolin-4(1H)-one was converted to quinolino[2′,3′:3,4]pyrazolo[5,1-b]quinazolin-8(6H)-ones in the presence of KOtBu in DMSO at room temperature. The present method has the advantages of easy conditions, construction of highly novel five heterocycles, transition metal-free conditions, cascade dehydrogenation and intramolecular N-arylation and good to high yield of products.

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Acknowledgments

We thank Alzahra University and Iran National Science Foundation (INSF) for financial support to our research group.

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Correspondence to Morteza Shiri or Majid M. Heravi.

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Shiri, M., Heravi, M.M., Hamidi, H. et al. Transition metal-free synthesis of quinolino[2′,3′:3,4]pyrazolo[5,1-b]quinazolin-8(6H)-ones via cascade dehydrogenation and intramolecular N-arylation. J IRAN CHEM SOC 13, 2239–2246 (2016). https://doi.org/10.1007/s13738-016-0942-7

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  • DOI: https://doi.org/10.1007/s13738-016-0942-7

Keywords

  • Quinoline
  • Quinazolinone
  • Intramolecular N-arylation
  • Cascade reaction
  • Polyheterocycles
  • Transition metal-free