Acceptorless Dehydrogenation under Neat Reaction Conditions: Synthesis of 2-Aryl/Alkyl Quinazolinones Using Supported Ni NPs as Catalyst

IF 1.7 4区 化学 Q3 CHEMISTRY, ORGANIC Synlett Pub Date : 2024-09-18 DOI:10.1055/a-2388-9487
Vageesh MM, Omkar Patil, Hima PP, Raju Dey
{"title":"Acceptorless Dehydrogenation under Neat Reaction Conditions: Synthesis of 2-Aryl/Alkyl Quinazolinones Using Supported Ni NPs as Catalyst","authors":"Vageesh MM, Omkar Patil, Hima PP, Raju Dey","doi":"10.1055/a-2388-9487","DOIUrl":null,"url":null,"abstract":"<p>We report here a Ni-NPs-catalyzed one-pot synthesis of 2-alkyl/aryl quinazolinone motifs <i>via</i> acceptorless dehydrogenation of alcohol, condensation of an aldehyde intermediate with 2-aminobenzamide, followed by a second dehydrogenation of the cyclized intermediate. The protocol is atom-economical and require earth-abundant Ni as the catalyst. The present report involves the annulation of 2-aminobenzamide with various types of primary alcohols, including aryl/heteroaryl methanol, and aliphatic alcohols, and produces high yields of the desired products under neat conditions. The catalyst was synthesized <i>via</i> a high-temperature pyrolysis strategy, using ZIF-8 as the sacrificial template. The Ni NPs@N-C catalyst was characterized by XPS, HR-TEM, HAADF-STEM, XRD, and ICP-MS. The catalyst is stable even in air at room temperature and displayed excellent activity in the acceptorless dehydrogenative coupling synthesis of quinazolinones and could be recycled five times without appreciable loss of its activity.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synlett","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1055/a-2388-9487","RegionNum":4,"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

Abstract

We report here a Ni-NPs-catalyzed one-pot synthesis of 2-alkyl/aryl quinazolinone motifs via acceptorless dehydrogenation of alcohol, condensation of an aldehyde intermediate with 2-aminobenzamide, followed by a second dehydrogenation of the cyclized intermediate. The protocol is atom-economical and require earth-abundant Ni as the catalyst. The present report involves the annulation of 2-aminobenzamide with various types of primary alcohols, including aryl/heteroaryl methanol, and aliphatic alcohols, and produces high yields of the desired products under neat conditions. The catalyst was synthesized via a high-temperature pyrolysis strategy, using ZIF-8 as the sacrificial template. The Ni NPs@N-C catalyst was characterized by XPS, HR-TEM, HAADF-STEM, XRD, and ICP-MS. The catalyst is stable even in air at room temperature and displayed excellent activity in the acceptorless dehydrogenative coupling synthesis of quinazolinones and could be recycled five times without appreciable loss of its activity.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
清洁反应条件下的无受体脱氢反应:以支撑镍氮氧化物为催化剂合成 2-芳基/烷基喹唑啉酮
我们在此报告了一种 Ni-NPs 催化的单锅合成 2-烷基/芳基喹唑啉酮基团的方法,该方法通过醇的无受体脱氢、醛中间体与 2- 氨基苯甲酰胺的缩合,然后对环化中间体进行第二次脱氢。该方案原子经济,需要地球上丰富的 Ni 作为催化剂。本报告涉及 2-氨基苯甲酰胺与各种类型的伯醇(包括芳基/杂芳基甲醇和脂肪醇)的环化反应,并在纯净条件下产生高产率的所需产物。该催化剂是以 ZIF-8 为牺牲模板,通过高温热解策略合成的。通过 XPS、HR-TEM、HAADF-STEM、XRD 和 ICP-MS 对 Ni NPs@N-C 催化剂进行了表征。该催化剂即使在室温空气中也很稳定,在喹唑啉酮类化合物的无受体脱氢偶联合成中表现出优异的活性,并且可以循环使用五次而不会明显降低其活性。
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 去求助
来源期刊
Synlett
Synlett 化学-有机化学
CiteScore
3.40
自引率
5.00%
发文量
369
审稿时长
1 months
期刊介绍: SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.
期刊最新文献
Sustainable N-Formylation of Anilines: Harnessing Aleuritic Acid as a Renewable Formyl Source Acceptorless Dehydrogenation under Neat Reaction Conditions: Synthesis of 2-Aryl/Alkyl Quinazolinones Using Supported Ni NPs as Catalyst Comparison of the Effects of Stirring and Standing on Chemical Reactions Nickel-Catalyzed O-Methylation of Cinnamic Acid Using DMSO as Methyl Surrogate Skeletal Reorganization: Approaches towards the Synthesis of Aza-Heterocyclic Cores
×
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
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 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 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1