Synthesis of 1,3-Disubstituted Hexahydropyrimidine Derivatives from Dibenzoylmethane, Acetylacetone, Ethyl Acetoacetate: One-Pot FeCl 3-Catalyzed Mannich Reaction

Abdullah Saleh, Martha Morton, John D'Angelo

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

1,3-Disubstituted hexahydropyrimidin-5-yl(phenyl)methanone (products 1-5) were prepared from the reaction of dibenzoylmethane with primary amines and formaldehyde in the presence of Lewis acid catalyst at ambient temperature. Replication of the reaction with acetylacetone and ethyl aetoacetate yielded 1,1′-(1,3-disubstituted hexahydropyrimidine-5,5-diyl)diethanone (products 6-10) and ethyl 5-acetylhexahydropyrimidine-5-carboxylate (products 11-13), respectively. Yields obtained ranged from 69 to 89%.

Original languageEnglish (US)
Pages (from-to)2715-2723
Number of pages9
JournalSynthetic Communications
Volume44
Issue number18
DOIs
StatePublished - Sep 17 2014

Keywords

  • Debenzoylation
  • Mannich reaction
  • hexahydropyrimidines

ASJC Scopus subject areas

  • Organic Chemistry

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