Three-component one-pot synthesis of novel pyrido[2,3-d]pyrimidine indole substituted derivatives and DFT analysis
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Pyridopyrimidines are heterocyclic aromatic compounds known by their antibacterial and medicinal properties. In this work, a series of pyrido[2,3-d]pyrimidine indole derivatives were synthesized by three-component one pot cyclocondensation Michael reaction between 2,6-diaminopirimidin-4(3H)-one, 3-(2-cyanoacetyl)indole and aromatic aldehydes in boiling acetic acid as solvent. The compounds differ with respect to the substituents of the aromatic aldehyde which are comprised by -C6H5, -4-ClC6H4, -4-NO2C6H4, -3,4-OCH2OC6H3, -3-OCH3,4-OH,5-NO2C6H2, and -3,4,5-tri-H3COC6H2, respectively. The compounds were synthesized with reasonable yields. They were characterized by and IR, mass, and NMR spectrometry. The protocol employed offers the convenient advantages of a one-step synthesis, considerable savings of solvents, and easy isolation of reaction products. In addition, DFT and TD-DFT quantum chemical calculations were used to characterize the geometry and electronic structure of the compounds. © 2017 Elsevier B.V.
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