An Efficient Procedure for the Synthesis of 2-Arylsubstituted Benzimidazoles Catalyzed by Co (II) Immobilized on Fe3O4@SiO2-NH2/EP@SAA as a Recyclable Nanomagnetic Catalyst

IF 1.2 4区 化学 Q4 CHEMISTRY, ORGANIC
Mohammad Nikbin , Ebrahim Mollashahi , Malek Taher Maghsoodlou , Mojtaba Lashkari
{"title":"An Efficient Procedure for the Synthesis of 2-Arylsubstituted Benzimidazoles Catalyzed by Co (II) Immobilized on Fe3O4@SiO2-NH2/EP@SAA as a Recyclable Nanomagnetic Catalyst","authors":"Mohammad Nikbin , Ebrahim Mollashahi , Malek Taher Maghsoodlou , Mojtaba Lashkari","doi":"10.1080/00304948.2023.2181622","DOIUrl":null,"url":null,"abstract":"Fast, simple and high-yield synthesis continues to be a major challenge for synthetic organic chemists. Among nitrogen-containing heterocyclic compounds, 1 the benzimidazole ring is an important pharmacophore for modern drug discovery. 2 Benzimidazoles have significant biological properties including anticancer, 3 anti-HIV, 4 antibacterial, 5 anti-ulcer, 6 anti-tumor 7 and enzyme inhibitory 8 properties. Benzimidazoles are also important intermediates in organic reactions. 9 Due to the importance of benzimidazoles, interest in the synthesis of these compounds has increased. The most common method is the condensation of o -aryldiamines and carbonyl compounds, especially aldehydes; and the wide availability of the latter makes this route particularly attractive for the production of 2-arylsubstituted benzimidazoles. 10 Numerous oxidative and catalytic reagents have been employed in this method, including Oxone, 11 In(OTf) 312 , FeCl 3 (cid:1) 6H 2 O, 13 I 2 /KI/K 2 CO 314 , sulfamic acid, 15 KHSO 416 , TBAF, 17 SBSA, 18 TiCl 3 OTf 19 and VOSO 4 . 20 These catalysts have been useful for their own purposes in facilitating the synthesis of the expected compounds. However, some of these methods have disadvantages such as high reaction temperatures, prolonged reaction times, low yields, expense, complex work-up procedures or toxic solvents. So the discovery of mild","PeriodicalId":19681,"journal":{"name":"Organic Preparations and Procedures International","volume":"55 5","pages":"Pages 444-451"},"PeriodicalIF":1.2000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Preparations and Procedures International","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0030494823000254","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

Fast, simple and high-yield synthesis continues to be a major challenge for synthetic organic chemists. Among nitrogen-containing heterocyclic compounds, 1 the benzimidazole ring is an important pharmacophore for modern drug discovery. 2 Benzimidazoles have significant biological properties including anticancer, 3 anti-HIV, 4 antibacterial, 5 anti-ulcer, 6 anti-tumor 7 and enzyme inhibitory 8 properties. Benzimidazoles are also important intermediates in organic reactions. 9 Due to the importance of benzimidazoles, interest in the synthesis of these compounds has increased. The most common method is the condensation of o -aryldiamines and carbonyl compounds, especially aldehydes; and the wide availability of the latter makes this route particularly attractive for the production of 2-arylsubstituted benzimidazoles. 10 Numerous oxidative and catalytic reagents have been employed in this method, including Oxone, 11 In(OTf) 312 , FeCl 3 (cid:1) 6H 2 O, 13 I 2 /KI/K 2 CO 314 , sulfamic acid, 15 KHSO 416 , TBAF, 17 SBSA, 18 TiCl 3 OTf 19 and VOSO 4 . 20 These catalysts have been useful for their own purposes in facilitating the synthesis of the expected compounds. However, some of these methods have disadvantages such as high reaction temperatures, prolonged reaction times, low yields, expense, complex work-up procedures or toxic solvents. So the discovery of mild
固定化Co(II)催化合成2-芳基取代苯并咪唑的有效方法Fe3O4@SiO2-NH2/EP@SAA作为一种可回收的纳米磁性催化剂
快速、简单和高产的合成仍然是合成有机化学家面临的主要挑战。在含氮杂环化合物中,苯并咪唑环是现代药物发现的重要药效团。2苯并咪唑具有显著的生物学特性,包括抗癌、3抗HIV、4抗菌、5抗溃疡、6抗肿瘤7和酶抑制8特性。苯并咪唑也是有机反应中的重要中间体。9由于苯并咪唑的重要性,人们对这些化合物的合成越来越感兴趣。最常见的方法是邻芳基二胺和羰基化合物,尤其是醛类化合物的缩合;后者的广泛可用性使得该路线对于2-芳基取代苯并咪唑的生产特别有吸引力。10在该方法中使用了许多氧化和催化试剂,包括Oxone、11In(OTf)312、FeCl3(cid:1)6H2O、13I2/KI/K2CO314、氨基磺酸、15KHSO416、TBAF、17SBSA、18TiCl3OTf19和VOSO4。20这些催化剂对于它们自身的目的在促进预期化合物的合成方面是有用的。然而,这些方法中的一些具有缺点,例如高反应温度、延长反应时间、低产率、费用、复杂的后处理程序或有毒溶剂。所以温和的发现
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
CiteScore
2.60
自引率
13.30%
发文量
60
审稿时长
2 months
期刊介绍: Organic Preparations and Procedures International (OPPI) publishes important, bimonthly research relevant to organic chemists engaged in synthesis. It is devoted to preparative organic chemistry, organometallic compounds, and procedures generally related to synthesis. The mission has always been to assist the practitioner by publishing reliable and reproducible procedures of the highest standards. OPPI publishes articles in every area of preparative organic chemistry - from innovative technology to improvements in traditional synthesis. Along with experimental papers, the Journal publishes authoritative reviews on significant topics in synthesis. The editors work closely with all authors, including those whose first language may not be English, to ensure important work is provided with clarity and a forum, giving OPPI a truly unique opportunity to serve a worldwide audience with valuable material.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信