A new synthetic approach to functionalize pyrimido[4,5-b]quinoline-2,4(1H,3H)-diones via a three-component one-pot reaction.
Functionalized pyrimido[4,5-b]quinoline-2,4 (1H,3H)-diones were synthesized by a three-component one-pot reaction involving barbituric acid, aldehydes, and anilines. The use of commercially available anilines allowed the facile syntheses of pyrimido[4,5-b]quinolinediones substituted in all the positions on the benzene ring with electron donor or electron withdrawing groups. This straightforward method circumvents the preparation of unstable substituted 2-aminobenzaldehydes that limits the scope of previously described syntheses. Furthermore, access to the 5-substituted derivatives is now also possible starting from aliphatic or aromatic aldehydes. Our strategy and methodology offer significant and practical improvements over other methodologies.
Aknin
Karen
K
Laboratoire de Chimie Thérapeutique, UMR CNRS N 8638, Université Paris Descartes, Faculté des Sciences, Pharmaceutiques et Biologiques, 4 avenue de l'Observatoire, 75270, Paris Cedex 06, France.
Desbène-Finck
Stéphanie
S
Helissey
Philippe
P
Giorgi-Renault
Sylviane
S
D019342:Acetic Acid / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D001463:Barbiturates / Q000737:chemistry; D055598:Chemical Phenomena; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
D000814:Aniline Compounds; D001463:Barbiturates; D011744:Pyrimidinones; D011804:Quinolines; D019342:Acetic Acid; C032232:barbituric acid