Synthesis of [1,2,3]Triazolo[1,5-a]quinoline-3-carboxamides Promoted by Organocatalyst and Base

We described here a simple and metal-free protocol to synthesize [1,2,3]triazolo[1,5-a]quinoline 3-carboxamides through a two-step synthetic strategy, in which the first step uses organocatalysis (10 mol % of diethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene, while the second step involves the use of inorganic base (1.2 or 0.1 equiv. of potassium hydroxide). These reactions were performed between & beta;-keto amides and o-carbonyl phenylazides in dimethylsulfoxide as solvent at 70 & DEG;C for 2 h. The synthetic protocol is ample, which thirteen examples of secondary [1,2,3]triazolo[1,5-a]quinoline 3-carboxamides were synthesized ranging from good to excellent yields (63-96 %), and six different tertiary [1,2,3]triazolo[1,5-a]quinolines 3-carboxamides were obtained ranging from moderate to good yields (48-76 %).

Automated summary

We described a simple and metal-free protocol for the synthesis of [1,2,3]triazolo[1,5-a]quinoline 3-carboxamides. The synthesis involves two steps, with the first step utilizing organocatalysis and the second step involving the use of an inorganic base. The reactions were performed in dimethylsulfoxide as solvent at 70°C for 2 hours. The synthetic protocol yielded a variety of [1,2,3]triazolo[1,5-a]quinoline 3-carboxamides in good to excellent yields (63-96%) for secondary compounds and moderate to good yields (48-76%) for tertiary compounds.