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Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5‐ a ]quinolines
Author(s) -
Costa Gabriel P.,
Bach Mariana F.,
Moraes Maiara C.,
Barcellos Thiago,
Lenardão Eder J.,
Silva Márcio S.,
Alves Diego
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000887
Subject(s) - chemistry , cycloaddition , quinoline , intramolecular force , intermolecular force , catalysis , ring (chemistry) , medicinal chemistry , solvent , triazole , condensation , one pot synthesis , condensation reaction , combinatorial chemistry , organic chemistry , molecule , physics , thermodynamics
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.