Efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones using heterogeneous solid acid catalysts: Unexpected formation of 2,3-dihydro-2-(4-(tetrahydro-2H- pyran-2-yloxy)butyl)quinazolin-4(1H)-one

Sandip B. Bharate, Nagaraju Mupparapu, Sudhakar Manda, Jaideep B. Bharate, Ramesh Mudududdla, Rammohan R. Yadav, Ram A. Vishwakarma

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20 Citations (Scopus)

Abstract

The heterogeneous solid acid catalysts Amberlyst-15 and silica-HClO 4 displays efficient catalytic properties for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones from anthranilamide and various aldehydes/ketones under mild reaction conditions and in good yields. These catalysts also showed good catalytic activity for condensation of anthranilamide with a cyclic enol ether 3,4-dihydropyran and led to formation of new unexpected quinazolinone product 6 comprising two dihydropyran moieties. The new product 6 has been reported for the first time and is fully characterized using 2D-NMR data. Furthermore, both solid acid catalysts can be easily recycled without significant loss of activity.

Original languageEnglish
Pages (from-to)308-318
Number of pages11
JournalARKIVOC
Volume2012
Issue number8
DOIs
Publication statusPublished - 26 Aug 2012
Externally publishedYes

Keywords

  • 2,3-dihydroquinazolin-4(1H)-ones
  • 3,4-dihydropyran
  • Aldehydes
  • Amberlyst-15
  • Heterogeneous catalysis
  • Ketones

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