Synthesis of 6-substituted 7-aryl-5,6-dihydropyrido[2,3-d]pyrimidine(1H,3H)-2,4-diones using the Vilsmeier reaction
- 作者：Girreser ; Ulrich ; Heber ; Dieter ; Schü ; tt ; Martin
- 关键词：Cyclization ; Cyclocondensation ; 6-Amino-1 ; 3-dimethyluracil ; Mannich bases ; Vilsmeier reaction ; Pyrido[2 ; 3-d]pyrimidines
- 刊名：Tetrahedron
- 出版年：2004
- 期刊代码：107_00404020
- 类别：ch
- 出版时间：December 6, 2004
- 卷：60
- 期：50
- 页码：11511-11517
- 文件大小：216 K
摘要
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(1H,3H)-2,4-diones with the Vilsmeier reagent affords, depending on the reaction conditions, either 6-dimethylaminomethylidene substituted 5H-pyrido[2,3-d]pyrimidine(1H,3H)-2,4-diones or the corresponding pyridopyrimidine(1H,3H)-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.