1913-55-9Relevant academic research and scientific papers
Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5-a]quinolines
Alves, Diego,Bach, Mariana F.,Barcellos, Thiago,Lenard?o, Eder J.,Silva, Márcio S.,da Costa, Gabriel P.,de Moraes, Maiara C.
, p. 5044 - 5055 (2020)
In this work, a one-pot sequential organocatalytic method for the synthesis of fused [1,2,3]triazolo[1,5-a]quinolines through successive cyclization and condensation is presented. In this synthetic strategy, the intermolecular [3+2]-cycloaddition occurs between 1,3-dicarbonyl compounds and o-carbonyl-substituted phenylazide compounds, for the formation of the 1,2,3-triazole intermediates. Subsequently, an intramolecular condensation reaction generates the fused quinoline ring by the new C?C bond formation, giving the products in yields ranging from moderate to excellent. All the reactions were performed using 20 mol% of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as catalyst in the presence of DMSO as solvent at 120 °C for 24 h and tolerate a range of 1,3-dicarbonyl compounds, such as β-keto esters and 1,3-diketones, and o-formyl, o-acetyl or o-benzoyl substituted phenylazide compounds. (Figure presented.).
