Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5‐a]quinolines,Advanced Synthesis & Catalysis

当前位置： X-MOL 学术 › Adv. Synth. Catal. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5‐a]quinolines
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-09-25 , DOI: 10.1002/adsc.202000887
Gabriel Costa ₁ , Mariana Bach ₁ , Maiara de Moraes ₂ , Thiago Barcellos da Silva ₂ , Eder Lenardao ₃ , Márcio Silva ₃ , Diego Alves ₄

Affiliation

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.

中文翻译：

[1,2,3]三唑并[1,5-a]喹啉的顺序有机催化合成

在这项工作中，提出了一种通过连续环化和缩合反应合成稠合[1,2,3]三唑并[1,5- a ]喹啉的单锅顺序有机催化方法。在这种合成策略中，分子间的[3 + 2]-环加成反应发生在1,3-二羰基化合物与邻羰基取代的苯叠氮化合物之间，从而形成1,2,3-三唑中间体。随后，分子内的缩合反应通过新的C-C键的形成生成稠合的喹啉环，从而使产物的收率从中等到极好。在DMSO作为溶剂存在下，使用20 mol％的1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）作为催化剂，在120°C下进行24 h，反应范围为1。，3-二羰基化合物，例如β-酮酸酯和1,3-二酮，以及邻甲酰基，邻乙酰基或邻苯甲酰基取代的苯叠氮化合物。

更新日期：2020-11-19

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11