Synthesis of 2-(hetero)arylquinazolinones in aqueous media

Magyar Tímea, Ferenc Miklós, László Lázár, Ferenc Fülöp

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Abstract

Mechanochemical treatment of N-unsubstituted or N-methyl anthranilamide with benzaldehyde yielded their Schiff bases derivatives which could be easily cyclized to the corresponding 2-phenyl-2,3-dihydroquinazolinones via thermal rearrangement in water. On the basis of the above findings, an eco-friendly method was applied to prepare quinazolin-4(1H)-one derivatives from anthranilamides and a number of (hetero)aryl aldehydes. Heating the aqueous mixture of starting compounds to 90 °C resulted in the products in 81-94% yields. All products precipitated from the reaction mixture and were isolated by simply filtration. No further work-up or purification was necessary.

Original languageEnglish
Pages (from-to)247-258
Number of pages12
JournalArkivoc
Volume2016
Issue number6
DOIs
Publication statusPublished - Jan 1 2016

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Keywords

  • Aqueous
  • Ball-milling reactions
  • Chromatography-free
  • Environmentally friendly methods
  • Mechanochemical

ASJC Scopus subject areas

  • Organic Chemistry

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