A new and practical method for the synthesis of 6-aryl-5,6-dihydropyrido[2, 3-d]pyrimidine-4,7(3H,8H)-diones

Marta Camarasa, Christian Barnils, Raimon Puig De La Bellacasa, Jordi Teixidó, José I. Borrell

Research output: Indexed journal article Articlepeer-review

10 Citations (Scopus)

Abstract

A one step general synthetic methodology for the synthesis of 6-aryl-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-diones (17{x} (G = NH 2) and 20{x } (G = SMe) is described. This methodology is based on reacting a 2-aryl-substituted acrylate (16{x}) with the corresponding 6-aminopyrimidin-4(3H) -one (13 (G=NH2)); 19 (G =SMe)) in presence of a base under microwave irradiation. The resulting pyrido[2,3-d ]pyrimidines present an aryl substituent at position C6, precisely the one directly related to the biological activity of such heterocycles. These protocols have been extended to other 2-alkyl-substituted and 3-alkyl (or aryl)-substituted acrylates but with lower yields.

Original languageEnglish
Pages (from-to)525-536
Number of pages12
JournalMolecular Diversity
Volume17
Issue number3
DOIs
Publication statusPublished - Aug 2013

Keywords

  • 2-Aryl acrylates
  • 4-Oxopyrido[2,3-d ]pyrimidines
  • 6-Aminopyrimidine-4 (3H) -ones
  • Michael addition
  • Pyrido[2,3-d ]pyrimidines

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