Synthesis of [1,2,3]Triazolo[1,5-a]quinoline-3-carboxamides Promoted by Organocatalyst and Base |
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| Authors: | Dr Gabriel P Da Costa Gustavo B Blödorn Prof?Dr Thiago Barcellos Prof?Dr Márcio S Silva Prof?Dr Rafael Luque Prof?Dr Diego Alves |
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| Institution: | 1. LASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil;2. Laboratory of Biotechnology of Natural, and Synthetic Products, Universidade de Caxias do Sul, Caxias do Sul, RS, Brazil;3. Peoples Friendship University of Russia, RUDN University), 6 Miklukho-Maklaya str., Moskva, 117198, Moscow Russia
Universidad ECOTEC, Km 13.5, Samborondón, Samborondón, EC 092302 Ecuador |
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| Abstract: | We described here a simple and metal-free protocol to synthesize 1,2,3]triazolo1,5-a]quinoline 3-carboxamides through a two-step synthetic strategy, in which the first step uses organocatalysis (10 mol % of diethylamine or 1,8-diazabicyclo5.4.0]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 β-keto amides and o-carbonyl phenylazides in dimethylsulfoxide as solvent at 70 °C for 2 h. The synthetic protocol is ample, which thirteen examples of secondary 1,2,3]triazolo1,5-a]quinoline 3-carboxamides were synthesized ranging from good to excellent yields (63-96 %), and six different tertiary 1,2,3]triazolo1,5-a]quinolines 3-carboxamides were obtained ranging from moderate to good yields (48–76 %). |
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| Keywords: | Carboxamide metal-free organocatalysis triazoles synthetic methods |
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