醋酸催化一锅法合成新型苯并[4,5]咪唑[1,2-a]嘧啶和吡唑[1,5-a]嘧啶

IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC
Najla Altwaijry , Asmaa Saleh , Esam A. Ishak , Hamdi M. D. Nasr , Ismail M. M. Othman
{"title":"醋酸催化一锅法合成新型苯并[4,5]咪唑[1,2-a]嘧啶和吡唑[1,5-a]嘧啶","authors":"Najla Altwaijry ,&nbsp;Asmaa Saleh ,&nbsp;Esam A. Ishak ,&nbsp;Hamdi M. D. Nasr ,&nbsp;Ismail M. M. Othman","doi":"10.1080/00397911.2024.2419872","DOIUrl":null,"url":null,"abstract":"<div><div>A novel set chalcones <strong>3a-d</strong> was efficiently synthesized in elevated produces across the condensing process of Claisen-Schmidt. An eco-friendly and efficient process was designed for creating a novel desired products <strong>5a-f</strong> and <strong>7a-f</strong>, respectively with excellent yields. This synthesis was accomplished by reacting acetophenone derivatives <strong>1a-d</strong>, heteroaromatic aldehydes <strong>2a,b</strong> and aminobenzoimidazole <strong>4</strong> or 3-aminopyrazole <strong>6a,b</strong>, using acetic acid as both the catalyst and solvent. Solvent optimization was performed during the synthesis of the desired compounds <strong>5a</strong> or <strong>7a</strong>, highlighting the benefits of using acetic acid that is harmless for the environment, which offers easy procedure, rapid reaction, elevated efficiency and broad tolerance of starting materials. The preferred products were verified through compatible spectroscopic data. The antimicrobial efficacious for all compounds was successfully evaluated against various microorganisms, revealing that <strong>3b</strong> exhibited significant antimicrobial activity across all tested microbes, with measurements of the minimum inhibitory concentrations being between 4.80 to 63.8 μM.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 23","pages":"Pages 2038-2051"},"PeriodicalIF":1.8000,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"One-pot synthesis of new benzo[4,5]imidazo[1,2-a]pyrimidines and pyrazolo[1,5-a] pyrimidines as an eco-friendly and effective method catalyzed by acetic acid with prospective antimicrobial agents\",\"authors\":\"Najla Altwaijry ,&nbsp;Asmaa Saleh ,&nbsp;Esam A. Ishak ,&nbsp;Hamdi M. D. Nasr ,&nbsp;Ismail M. M. Othman\",\"doi\":\"10.1080/00397911.2024.2419872\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A novel set chalcones <strong>3a-d</strong> was efficiently synthesized in elevated produces across the condensing process of Claisen-Schmidt. An eco-friendly and efficient process was designed for creating a novel desired products <strong>5a-f</strong> and <strong>7a-f</strong>, respectively with excellent yields. This synthesis was accomplished by reacting acetophenone derivatives <strong>1a-d</strong>, heteroaromatic aldehydes <strong>2a,b</strong> and aminobenzoimidazole <strong>4</strong> or 3-aminopyrazole <strong>6a,b</strong>, using acetic acid as both the catalyst and solvent. Solvent optimization was performed during the synthesis of the desired compounds <strong>5a</strong> or <strong>7a</strong>, highlighting the benefits of using acetic acid that is harmless for the environment, which offers easy procedure, rapid reaction, elevated efficiency and broad tolerance of starting materials. The preferred products were verified through compatible spectroscopic data. The antimicrobial efficacious for all compounds was successfully evaluated against various microorganisms, revealing that <strong>3b</strong> exhibited significant antimicrobial activity across all tested microbes, with measurements of the minimum inhibitory concentrations being between 4.80 to 63.8 μM.</div></div>\",\"PeriodicalId\":22119,\"journal\":{\"name\":\"Synthetic Communications\",\"volume\":\"54 23\",\"pages\":\"Pages 2038-2051\"},\"PeriodicalIF\":1.8000,\"publicationDate\":\"2024-12-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthetic Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S0039791124001267\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0039791124001267","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

摘要

在clisen - schmidt缩合过程中,以高收率合成了一组新的查尔酮3a-d。设计了一种环保和高效的工艺,分别用于生产新的所需产品5a-f和7a-f,收率很高。以乙酸为催化剂和溶剂,苯乙酮衍生物1a-d、杂芳醛2a、b和氨基苯并咪唑4或3-氨基吡唑6a、b为反应原料合成了该化合物。在合成所需化合物5a或7a的过程中,对溶剂进行了优化,突出了使用乙酸对环境无害的优点,它具有操作简单、反应快速、效率高和对起始原料耐受性广的优点。通过兼容的光谱数据对优选产物进行了验证。对所有化合物的抑菌效果进行了成功的评估,结果表明3b对所有被测微生物都具有显著的抑菌活性,最小抑菌浓度在4.80 ~ 63.8 μM之间。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
One-pot synthesis of new benzo[4,5]imidazo[1,2-a]pyrimidines and pyrazolo[1,5-a] pyrimidines as an eco-friendly and effective method catalyzed by acetic acid with prospective antimicrobial agents
A novel set chalcones 3a-d was efficiently synthesized in elevated produces across the condensing process of Claisen-Schmidt. An eco-friendly and efficient process was designed for creating a novel desired products 5a-f and 7a-f, respectively with excellent yields. This synthesis was accomplished by reacting acetophenone derivatives 1a-d, heteroaromatic aldehydes 2a,b and aminobenzoimidazole 4 or 3-aminopyrazole 6a,b, using acetic acid as both the catalyst and solvent. Solvent optimization was performed during the synthesis of the desired compounds 5a or 7a, highlighting the benefits of using acetic acid that is harmless for the environment, which offers easy procedure, rapid reaction, elevated efficiency and broad tolerance of starting materials. The preferred products were verified through compatible spectroscopic data. The antimicrobial efficacious for all compounds was successfully evaluated against various microorganisms, revealing that 3b exhibited significant antimicrobial activity across all tested microbes, with measurements of the minimum inhibitory concentrations being between 4.80 to 63.8 μM.
求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
Synthetic Communications
Synthetic Communications 化学-有机化学
CiteScore
4.40
自引率
4.80%
发文量
156
审稿时长
4.3 months
期刊介绍: Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.
×
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