Synthesis of 6-substituted 7-aryl-5,6-dihydropyrido[2,3-d]pyrimidine(1H,3H)-2,4-diones using the Vilsmeier reaction |
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Authors: | Ulrich Girreser Dieter Heber Martin Schütt |
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Institution: | Pharmazeutisches Institut, University of Kiel, Gutenbergstr. 76, 24118 Kiel, Germany |
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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-dihydropyrido2,3-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-pyrido2,3-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 pyrido2,3-d]pyrimidine derivatives. |
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Keywords: | Cyclization Cyclocondensation 6-Amino-1 3-dimethyluracil Mannich bases Vilsmeier reaction Pyrido[2 3-d]pyrimidines |
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