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Journal of Chemical Sciences

, Volume 124, Issue 5, pp 1033–1041 | Cite as

Substituted quinolinones. Part 17: Some nucleophilic reactions with 4-hydroxy-1-methyl-3-[(2-oxo-2H-chromen-3-yl)carbonyl]quinolin-2(1H)-one

  • Mohamed AbassEmail author
  • El-Hussain A Mohamed
  • Aisha S Mayas
  • Akram H Ibrahim
Article

Abstract

The reactivity of 4-hydroxy-1-methyl-3-[(2-oxo-2H-chromen-3-yl)carbonyl]-quinolin-2(1H)-one (2), as a new asymmetric diheterocyclic ketone, towards different nucleophilic reagents, was examined. The reaction of the ketone 2 with hydrazine led to pyrazolinone 5, and excess of hydrazine pyrazolinopyrazole 7 was obtained. Treatment of the ketone 2 with 2,2-dimethoxyethanamine gave pyrrolocoumarin 12, while cyanoguanidine afforded pyrimidinone 15. Under PTC conditions, the ketone 2 was reacted with chloroacetonitrile, diethyl malonate, ethyl cyanoacetate, malononitrile, and cyanoacetamide to give coumarinyl furoquinoline 18, pyranoquinolines 20a, 20b, 21, and benzonaphthyridine 22, respectively.

Graphical Abstract

The reaction of 3-[(chromon-3-yl)carbonyl]quinolin-2-one 2 towards nucleophiles, such as; hydrazine, 2,2-dimethoxyethanamine, cyanoguanidine, chloroacetonitrile, diethyl malonate, ethyl cyanoacetate, malononitrile, and cyanoacetamide was described leading to pyrazolines 5 and 7. pyrrolocoumarin 12, pyrimidinone 15, coumarinylfuroquinoline 18, pyranoquinolines 2021, and benzonaphthyridine 22, respectively.

Keywords

Quinolinone coumarin ketones nucleophilic heterocyclization PTC 

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Copyright information

© Indian Academy of Sciences 2012

Authors and Affiliations

  • Mohamed Abass
    • 1
    Email author
  • El-Hussain A Mohamed
    • 1
  • Aisha S Mayas
    • 2
  • Akram H Ibrahim
    • 3
  1. 1.Department of Chemistry, Faculty of EducationAin Shams UniversityCairoEgypt
  2. 2.Department of Chemistry, Faculty of EducationSana’a UniversitySana’aYemen
  3. 3.Curriculum Development Center, Ministry of EducationCairoEgypt

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