An environmentally friendly method for the synthesis of 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines in water promoted by potassium, sodium and ammonium chlorides

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2024-10-30 DOI:10.1016/j.tetlet.2024.155348

Natalia N. Gibadullina , Aigul R. Mukhamedyarova , Aleksandr N. Lobov , Yuri S. Zimin , Vladimir A. Dokichev

引用次数: 0

Abstract

A new one-pot method was developed for the synthesis of polyfunctional 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines by three-component reaction of ethyl 3-oxobutanoate with formaldehyde and primary amines occurring in water in the presence of electrolytes (NaCl, KCl, NH₄Cl) at room temperature. This environmentally friendly method is highly atom economic, because the only by-products it gives are three water molecules. The effect of the structure of primary amines and reaction conditions on the degree of formation of 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines was investigated.

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一种在钾、钠和铵氯化物促进下在水中合成 1,2,3,4-四氢吡啶和六氢咪唑并[1,2-a]吡啶的环保型方法

在室温下，通过 3-氧代丁酸乙酯与甲醛和伯胺在水中发生的三组分反应，在电解质（NaCl、KCl、NH4Cl）的存在下，开发了一种新的单锅法合成多官能团 1,2,3,4-四氢吡啶和六氢咪唑并[1,2-a]吡啶。这种对环境友好的方法具有很高的原子经济性，因为它唯一的副产品就是三个水分子。研究了伯胺结构和反应条件对 1,2,3,4 四氢吡啶和六氢咪唑并[1,2-a]吡啶形成程度的影响。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.