ArticleMolecular diversity2012
Synthesis of 2-arylamino substituted 5,6-dihydropyrido[2,3-d]pyrimidine-7(8H)-ones from arylguanidines.
Article in Molecular diversity, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed.
- The Use of a Penta-Deuterophenyl Substituent to Improve the Metabolic Stability of a Tyrosine Kinase Inhibitor.Molecules (Basel, Switzerland) · 2024Article
- Developments of pyridodipyrimidine heterocycles and their biological activities.Molecular diversity · 2024Review
- The Dimroth Rearrangement in the Synthesis of Condensed Pyrimidines - Structural Analogs of Antiviral Compounds.Chemistry of heterocyclic compounds · 2021Article
- Pyrido[2,3-Molecules (Basel, Switzerland) · 2019Review
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6 authors.
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Abstract
A practical protocol was developed for the synthesis of 2-arylamino substituted 4-amino-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-ones from α,β-unsaturated esters, malononitrile, and an aryl substituted guanidine via the corresponding 3-aryl-3,4,5,6- tetrahydropyrido[2,3-d]pyrimidin-7(8H)-ones. Such compounds are formed upon treatment of 2-methoxy-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitriles with an aryl substituted guanidine in 1,4-dioxane and are converted to the desired 4-aminopyridopyrimidines with NaOMe/MeOH through a Dimroth rearrangement. The overall yields of this three-step protocol are, generally speaking, higher than the multicomponent reaction, previously developed by our group, between an α,β-unsaturated ester, malononitrile, and an aryl substituted guanidine.
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