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藻酸:一种温和且可再生的双功能异质生物聚合物有机催化剂,用于高效、简便地合成多氢喹啉。

Alginic acid: A mild and renewable bifunctional heterogeneous biopolymeric organocatalyst for efficient and facile synthesis of polyhydroquinolines.

机构信息

Pharmaceutical and Heterocyclic Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Iran.

Pharmaceutical and Heterocyclic Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Iran.

出版信息

Int J Biol Macromol. 2018 Mar;108:1273-1280. doi: 10.1016/j.ijbiomac.2017.11.050. Epub 2017 Nov 12.

Abstract

Alginic acid, a widely used naturally occurring carbohydrate which is generally derived from brown seaweeds, can be considered as a bifunctional heterogeneous and green biopolymeric organocatalyst. Alginic acid, without any post-modification with active Bronsted or Lewis acid centers, was found to be a highly active, cost-effective, commercially-available, renewable and recoverable heterogeneous biopolymeric organocatalyst for the expeditious synthesis of polyhydroquinolines (PHQs). Polyhydroquinolines were synthesized from the four-component Hantzsch reaction of ethyl acetoacetate, different aldehydes, ammonium acetate and cyclic 1,3-diones under mild conditions in high to quantitative yields, 75-97%, using alginic acid. Furthermore, alginic acid was found to be reusable for at least 6 consecutive cycles without considerable loss of its catalytic activity.

摘要

海藻酸是一种广泛使用的天然存在的碳水化合物,通常从褐藻中提取,可被视为一种具有双重功能的异质和绿色生物聚合物有机催化剂。海藻酸未经任何带有活性布朗斯特或路易斯酸中心的后修饰,被发现是一种高效、经济实惠、商业上可获得、可再生和可回收的异质生物聚合物有机催化剂,可快速合成多氢喹啉(PHQs)。多氢喹啉是通过乙基乙酰乙酸酯、不同醛、醋酸铵和环状 1,3-二酮的四组分 Hantzsch 反应,在温和条件下以高至定量收率(75-97%)合成的,使用海藻酸。此外,海藻酸在至少 6 个连续循环中可重复使用,而其催化活性没有明显损失。

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