U. Girreser, D. Heber, Martin Schütt
Dec 6, 2004
Citations
0
Influential Citations
26
Citations
Journal
Tetrahedron
Abstract
Abstract The reaction of 6-amino-1,3-dimethyluracil with equimolar amounts of arylalkanone Mannich bases under optimized reaction conditions leads to 7-aryl-5,6-dihydropyrido[2,3- d ]pyrimidines in a yield of 50–80%. Functionalization of these dihydropyridopyrimidine(1 H ,3 H )-2,4-diones with the Vilsmeier reagent affords, depending on the reaction conditions, either 6-dimethylaminomethylidene substituted 5 H -pyrido[2,3- d ]pyrimidine(1 H ,3 H )-2,4-diones or the corresponding pyridopyrimidine(1 H ,3 H )-2,4-diones bearing a carboxaldehyde function in position 6 of the heterocycle. Some further transformations of the aldehyde function demonstrate the synthetic potential of the synthesized structures, introducing pharmacologically relevant basic substituents into the side chain of these pyrido[2,3- d ]pyrimidine derivatives.