Three-component one-pot synthesis of novel pyrido[2,3-d]pyrimidine indole substituted derivatives and DFT analysis
Autor
Rangel J.
Díaz-Uribe C.
Rodriguez-Serrano A.
Zarate X.
Serge Y.
Vallejo W.
Nogueras M.
Trilleras J.
Quiroga J.
Tatchen J.
Cobo J.
Resumen
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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