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聚离子磁性纳米粒子作为催化剂在协同双位 vinylogous 端基基于变旋的糖基氧化下合成同时含吲哚和三唑片段的碳腈

Application of polyionic magnetic nanoparticles as a catalyst for the synthesis of carbonitriles with both indole and triazole moieties via a cooperative geminal-vinylogous anomeric-based oxidation.

机构信息

Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, 6517838683, Hamedan, Iran.

出版信息

Mol Divers. 2022 Oct;26(5):2407-2426. doi: 10.1007/s11030-021-10339-8. Epub 2021 Oct 25.

Abstract

Three-component reaction of aldehydes with 3-(1H-indol-3-yl)-3-oxopropanenitrile and 1H-1,2,4-triazol-5-amine under the solvent-free condition at 70 °C was effectively performed in the presence of 2 mg of polyionic magnetic nanoparticles with pyrazine bridge [FeO@SiO@(CH)]-Pyrazinium-[TCM] as a catalyst for the synthesis of 7-aryl-5-(1H-indol-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles via a cooperative anomeric-based oxidation. The polyionic magnetic nanoparticles catalyst was simply recovered and reused four successive runs. The morphology and structure of MNPs catalyst were investigated by numerous techniques such as XRD, FT-IR, EDX, WDX, FE-SEM, TEM, TGA, DTA, and VSM. The obtained products are reported for the first time that were identified by various analyses techniques such as melting point, FT-IR, H NMR, C NMR, and elemental analysis (CHN). A term entitled a cooperative geminal-vinylogous anomeric-based oxidation was introduced for the latter step of the reaction mechanism for the first time. Synthesis of 7-aryl-5-(1H-indol-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles by using [FeO@SiO@(CH)]-Pyrazinium-[TCM] MNPs as a catalyst.

摘要

在无溶剂条件下,醛与 3-(1H-吲哚-3-基)-3-氧代丙腈和 1H-1,2,4-三唑-5-胺在 70°C 下反应,在 2mg 具有吡嗪桥的聚离子磁性纳米粒子[FeO@SiO@(CH)]-Pyrazinium-[TCM]作为催化剂的存在下,有效地进行了[1,2,4]三唑并[1,5-a]嘧啶-6-甲腈的合成,通过协同端基基于氧化。聚离子磁性纳米粒子催化剂被简单地回收并在四个连续的运行中重复使用。通过 XRD、FT-IR、EDX、WDX、FE-SEM、TEM、TGA、DTA 和 VSM 等多种技术研究了 MNPs 催化剂的形态和结构。首次报道了通过各种分析技术(如熔点、FT-IR、H NMR、C NMR 和元素分析(CHN))鉴定的产物。首次提出了协同双乙烯基端基基于氧化的术语,用于反应机制的后一步。使用[FeO@SiO@(CH)]-Pyrazinium-[TCM] MNPs 作为催化剂合成 7-芳基-5-(1H-吲哚-3-基)-[1,2,4]三唑并[1,5-a]嘧啶-6-甲腈。

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