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Research on Chemical Intermediates

, Volume 46, Issue 1, pp 165–177 | Cite as

An efficient and novel protocol for the synthesis of spiro[1,3]oxazino[5,6-c]quinoline derivatives by one-pot, three-component reaction

  • Maryam Aslanpanjeh
  • Ahmad Poursattar MarjaniEmail author
  • Jabbar Khalafy
  • Nasser Etivand
Article
  • 58 Downloads

Abstract

One-pot, three-component reaction of various aryl glyoxal monohydrates, 5-methylisoxazol-3-amine and 4-hydroxyquinolin-2(1H)-one in the presence of a catalytic amount of DBU in H2O/EtOH (1:1) at 50 °C produced the 4-aroyl-5′-methyl-3,4-dihydro-2′H-spiro[[1,3]oxazino[5,6-c]quinoline-2,3′-isoxazol]-5(6H)-one derivatives containing spiro[1,3]oxazino[5,6-c]quinoline moiety in 82–89% yield. The high yields of products, easy work-up, and availability of starting materials are the main advantages of this synthetic strategy.

Graphic abstract

Keywords

Aryl glyoxal monohydrates DBU 4-Hydroxyquinolin-2(1H)-one 5-Methylisoxazol-3-amine One-pot Three-component reaction Spiro heterocyclic compounds 

Notes

Acknowledgements

The authors gratefully acknowledge the financial support from Urmia University.

Supplementary material

11164_2019_3941_MOESM1_ESM.pdf (2 mb)
Supplementary material 1 (PDF 2140 kb)

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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  • Maryam Aslanpanjeh
    • 1
  • Ahmad Poursattar Marjani
    • 1
    Email author
  • Jabbar Khalafy
    • 1
  • Nasser Etivand
    • 1
  1. 1.Department of Organic Chemistry, Faculty of ChemistryUrmia UniversityUrmiaIran

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