Zn catalyzed a simple and convenient method for thiourea synthesis

IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Siddhanath D. Bhosle , Krishna A. Jadhav , Shivanand V. Itage , Sateesh Bandaru , Rajesh S. Bhosale , Jhillu Singh Yadav
{"title":"Zn catalyzed a simple and convenient method for thiourea synthesis","authors":"Siddhanath D. Bhosle ,&nbsp;Krishna A. Jadhav ,&nbsp;Shivanand V. Itage ,&nbsp;Sateesh Bandaru ,&nbsp;Rajesh S. Bhosale ,&nbsp;Jhillu Singh Yadav","doi":"10.1080/17415993.2022.2126319","DOIUrl":null,"url":null,"abstract":"<div><p>A straightforward and convenient synthesis of symmetrical and unsymmetrical thiourea derivatives by the reaction of primary amines and carbon disulfide in the presence of a Zn catalyst is presented. Under modest reaction conditions, a range of biologically relevant thiourea derivatives can be produced in good to outstanding yields without a lengthy work-up. A variety of primary aliphatic and aromatic amines with various substituted functional groups were transformed into thiourea derivatives. Zn-mediated symmetric thiourea creation occurs at room temperature for aliphatic amines, whereas for aromatic amines it occurs at 60°C. However, unsymmetrical thiourea for aliphatic amines occurs at 0°C. Benefits of this method include environment-friendly reaction conditions, sustainability, and enumerating tolerance of functional groups such as hydroxyl and halides. Experimental observations were rationalized by DFT calculations based on transition structures and zwitterionic intermediate stabilities.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 2","pages":"Pages 186-200"},"PeriodicalIF":2.1000,"publicationDate":"2023-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"2","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Sulfur Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1741599323000557","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 2

Abstract

A straightforward and convenient synthesis of symmetrical and unsymmetrical thiourea derivatives by the reaction of primary amines and carbon disulfide in the presence of a Zn catalyst is presented. Under modest reaction conditions, a range of biologically relevant thiourea derivatives can be produced in good to outstanding yields without a lengthy work-up. A variety of primary aliphatic and aromatic amines with various substituted functional groups were transformed into thiourea derivatives. Zn-mediated symmetric thiourea creation occurs at room temperature for aliphatic amines, whereas for aromatic amines it occurs at 60°C. However, unsymmetrical thiourea for aliphatic amines occurs at 0°C. Benefits of this method include environment-friendly reaction conditions, sustainability, and enumerating tolerance of functional groups such as hydroxyl and halides. Experimental observations were rationalized by DFT calculations based on transition structures and zwitterionic intermediate stabilities.

锌催化合成硫脲的一种简便方法
介绍了在锌催化剂存在下,伯胺与二硫化碳反应合成对称和不对称硫脲衍生物的简便方法。在适度的反应条件下,可以在不需要长时间处理的情况下以良好到卓越的产率生产一系列与生物学相关的硫脲衍生物。将各种具有不同取代官能团的伯脂族胺和芳香族胺转化为硫脲衍生物。对于脂肪族胺,锌介导的对称硫脲的产生在室温下发生,而对于芳香族胺,它在60°C下发生。然而,脂族胺的不对称硫脲发生在0°C。这种方法的优点包括环境友好的反应条件、可持续性和列举羟基和卤化物等官能团的耐受性。基于过渡结构和两性离子中间体稳定性的DFT计算使实验观察结果合理化。图形摘要
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
Journal of Sulfur Chemistry
Journal of Sulfur Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
4.10
自引率
9.10%
发文量
38
审稿时长
6-12 weeks
期刊介绍: The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science. Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.
×
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