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

被引：1

作者：

Da Costa, Gabriel P. P. ^{[1
]}

Blodorn, Gustavo B. B. ^{[1
]}

Barcellos, Thiago ^{[2
]}

Silva, Marcio S. ^{[1
]}

Luque, Rafael ^{[3
,4
]}

Alves, Diego ^{[1
]}

机构：

[1] Univ Fed Pelotas, LASOL, CCQFA, UFPel, POB 354, BR-96010900 Pelotas, RS, Brazil

[2] Univ Caxias do Sul, Lab Biotechnol Nat & Synthet Prod, Caxias Do Sul, RS, Brazil

[3] Peoples Friendship Univ Russia, RUDN Univ, 6 Miklukho Maklaya Str, Moscow 117198, Moscow, Russia

[4] Univ ECOTEC, Km 13-5 Samborondon, EC-092302 Samborondon, Ecuador

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 30期

关键词：

Carboxamide; metal-free; organocatalysis; triazoles; synthetic methods; METAL-FREE SYNTHESIS; EFFICIENT SYNTHESIS; ARYL AZIDES; CYCLOADDITION; 1,2,3-TRIAZOLES; QUINOLINE; HYBRIDS; DERIVATIVES; CASCADE; KETONES;

D O I：

10.1002/ejoc.202300604

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 %).

引用

页数：8

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