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水相超声合成四唑嘧啶衍生物的绿色化学:新型核壳磁性纳米结构催化剂。

Green in water sonochemical synthesis of tetrazolopyrimidine derivatives by a novel core-shell magnetic nanostructure catalyst.

机构信息

Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran.

Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran.

出版信息

Ultrason Sonochem. 2018 May;43:262-271. doi: 10.1016/j.ultsonch.2017.12.047. Epub 2017 Dec 27.

DOI:10.1016/j.ultsonch.2017.12.047
PMID:29555283
Abstract

A green approach for the one-pot four-component sonochemical synthesis of 5-methyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylic esters from the reaction of 2-cyano-guanidine, sodium azide, various aromatic aldehydes and methyl or ethyl acetoacetate in the presence of a catalytic amount of FeO@SiO-(CH)NHC(O)(CH)PPh as a new hybrid organic-inorganic core-shell nanomagnetic catalyst is described. This is the first design, preparation, characterization and application of the present nanomaterial and also the first ultrasound irradiated synthesis of the biologically and pharmaceutically important heterocyclic compounds in water as a green solvent. This novel sonocatalysis/nanocatalysis protocol offers several advantages such as high yields, short reaction times, environmentally-friendly reaction media, easily isolation of the products, simple preparation, full characterization and recoverability of the nanocatalyst by an external magnet and reusing several times without significant loss of activity.

摘要

一种绿色方法,用于一锅四组分超声化学合成 5-甲基-7-芳基-4,7-二氢四唑并[1,5-a]嘧啶-6-羧酸酯,反应原料为 2-氰基胍、叠氮化钠、各种芳醛和乙酰乙酸甲酯,在催化量的 FeO@SiO-(CH)NHC(O)(CH)PPh 的存在下,作为一种新型的混合有机-无机核壳纳米磁性催化剂。这是该纳米材料的首次设计、制备、表征和应用,也是首次在超声辐射下以水为绿色溶剂合成具有生物和药物重要性的杂环化合物。这种新颖的声催化/纳米催化方案具有许多优点,如高收率、短反应时间、环境友好的反应介质、产物易于分离、制备简单、纳米催化剂通过外部磁铁可完全表征和回收,并可重复使用数次而活性无明显损失。

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