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

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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.

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 20–21, and benzonaphthyridine 22, respectively.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Heliopolis 11757, Cairo, Egypt

    Mohamed Abass & El-Hussain A Mohamed

  2. Department of Chemistry, Faculty of Education, Sana’a University, Sana’a, Yemen

    Aisha S Mayas

  3. Curriculum Development Center, Ministry of Education, Ramsis, 13411, Cairo, Egypt

    Akram H Ibrahim

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  1. Mohamed Abass
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  2. El-Hussain A Mohamed
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  3. Aisha S Mayas
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  4. Akram H Ibrahim
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Correspondence to Mohamed Abass.

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Abass, M., Mohamed, EH.A., Mayas, A.S. et al. Substituted quinolinones. Part 17: Some nucleophilic reactions with 4-hydroxy-1-methyl-3-[(2-oxo-2H-chromen-3-yl)carbonyl]quinolin-2(1H)-one. J Chem Sci 124, 1033–1041 (2012). https://doi.org/10.1007/s12039-012-0303-8

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  • DOI: https://doi.org/10.1007/s12039-012-0303-8

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