"Dry" and "wet" green synthesis of 2,2′ -disubstituted quinazolinones

Ferenc Miklós, Ferenc Fülöp

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19 Citations (Scopus)

Abstract

An extremely convenient, environmentally benign spirocyclization under either aqueous or solventless conditions, developed for the preparation of spiro[cyclohexane-l,2′(l′H)-quinazolin]-4′(3′H)-one (3), has been utilized to convert α- and β-aminocarboxamides 5a, 5b, 6a-c and 9 and cycloalkanones 2-2b and alkanones 2c-e into 1,4-diazaspiro[4.5]decan- 2-one (10) and cis-, diexo- or diendo-2,2′-disub-stituted quinazolinones 5a, 5b, 7a-f and 8. diexo-Methylenebridged carboxamides 6a and 6b were treated "on water" with N-benzylpiperidinone (11) to afford spiropiperidinequinazolinones 12a and 12b. All these reactions were performed at room temperature, without any catalyst or co-solvent, and gave yields of up to 99%.

Original languageEnglish
Pages (from-to)959-965
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number5
DOIs
Publication statusPublished - Feb 1 2010

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Keywords

  • Green chemistry
  • Nitrogen heterocycles
  • Spiro compounds
  • Sustainable chemistry
  • Water chemistry

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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