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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/124/05/1033-1041

    • Keywords

       

      Quinolinone; coumarin; ketones; nucleophilic heterocyclization; PTC.

    • 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.

    • Author Affiliations

       

      Mohamed Abass1 El-Hussain A Mohamed1 Aisha S Mayas2 Akram H Ibrahim3

      1. Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Heliopolis 11757, Cairo, Egypt
      2. Department of Chemistry, Faculty of Education, Sana’a University, Sana’a, Yemen
      3. Curriculum Development Center, Ministry of Education, Ramsis 13411 Cairo, Egypt

    • Dates

       
      Published
      September 2012
      Manuscript received
      8 November 2011
      Manuscript revised
      4 April 2012
      Accepted
      26 April 2012

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