制备吡啶基离子液体并将其用作 4H-1-苯并吡喃-5(6H)-酮合成路线的绿色催化剂

Huong Ngoc Thi Dao, T. Nguyen, Tran Huyen Thi Nguyen, Thuy Hong Ngoc Phan, Phuong Hoang Tran
{"title":"制备吡啶基离子液体并将其用作 4H-1-苯并吡喃-5(6H)-酮合成路线的绿色催化剂","authors":"Huong Ngoc Thi Dao, T. Nguyen, Tran Huyen Thi Nguyen, Thuy Hong Ngoc Phan, Phuong Hoang Tran","doi":"10.31276/vjste.66(1).34-45","DOIUrl":null,"url":null,"abstract":"1-(4-sulfobutyl)pyridinium chlorozincate ionic liquid was synthesised in high yield (89%) through a simple route and characterised using FT-IR, NMR, and HRMS spectroscopy. The one-pot reaction was employed for the condensation reaction of benzaldehydes, 5,5-dimethyl-1,3-cyclohexanedione, and dicyanomethane, utilising the prepared ionic liquid catalyst. The optimal conditions for the reaction were achieved with a catalyst loading of 10 mol%, a solvent mixture of water and ethanol (1:1, v/v), maintained at 100°C for 180 minutes. A broad spectrum of benzopyran-5(6H)-one derivatives was prepared, yielding moderate to good results. The notable features of this procedure include readily available substrates, short reaction times, the use of environmentally friendly solvents, and the elimination of the need for chromatography in the isolation of products. Anew acidic pyridinium-based ionic liquid was successfully synthesised and used as a catalyst in the synthetic process of 2-amino-3-cyano-4-phenyl-7,7-dimethyl-7,8-dihydro-4H-1-benzopyran-5(6H)-ones. These reactions involved a condensation reaction of aromatic benzaldehydes, 5,5-dimethyl-1,3-cyclohexanedione, and dicyanomethane in a solvent mixture of ethanol and water, resulting in the desired products in moderate to good yields. The procedure is efficient and eco-friendly, and the products can be easily obtained by recrystallisation. Thus, this protocol offers an alternative to existing methods.","PeriodicalId":18650,"journal":{"name":"Ministry of Science and Technology, Vietnam","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2024-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Preparation of pyridinium-based ionic liquid and application as a green catalyst for the synthetic route of 4H-1-benzopyran-5(6H)-ones\",\"authors\":\"Huong Ngoc Thi Dao, T. Nguyen, Tran Huyen Thi Nguyen, Thuy Hong Ngoc Phan, Phuong Hoang Tran\",\"doi\":\"10.31276/vjste.66(1).34-45\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"1-(4-sulfobutyl)pyridinium chlorozincate ionic liquid was synthesised in high yield (89%) through a simple route and characterised using FT-IR, NMR, and HRMS spectroscopy. The one-pot reaction was employed for the condensation reaction of benzaldehydes, 5,5-dimethyl-1,3-cyclohexanedione, and dicyanomethane, utilising the prepared ionic liquid catalyst. The optimal conditions for the reaction were achieved with a catalyst loading of 10 mol%, a solvent mixture of water and ethanol (1:1, v/v), maintained at 100°C for 180 minutes. A broad spectrum of benzopyran-5(6H)-one derivatives was prepared, yielding moderate to good results. The notable features of this procedure include readily available substrates, short reaction times, the use of environmentally friendly solvents, and the elimination of the need for chromatography in the isolation of products. Anew acidic pyridinium-based ionic liquid was successfully synthesised and used as a catalyst in the synthetic process of 2-amino-3-cyano-4-phenyl-7,7-dimethyl-7,8-dihydro-4H-1-benzopyran-5(6H)-ones. These reactions involved a condensation reaction of aromatic benzaldehydes, 5,5-dimethyl-1,3-cyclohexanedione, and dicyanomethane in a solvent mixture of ethanol and water, resulting in the desired products in moderate to good yields. The procedure is efficient and eco-friendly, and the products can be easily obtained by recrystallisation. Thus, this protocol offers an alternative to existing methods.\",\"PeriodicalId\":18650,\"journal\":{\"name\":\"Ministry of Science and Technology, Vietnam\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-03-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Ministry of Science and Technology, Vietnam\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.31276/vjste.66(1).34-45\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Ministry of Science and Technology, Vietnam","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.31276/vjste.66(1).34-45","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

摘要

通过简单的方法合成了 1-(4-磺丁基)吡啶鎓氯锌酸盐离子液体,收率高达 89%,并利用傅立叶变换红外光谱、核磁共振和 HRMS 光谱对其进行了表征。利用制备的离子液体催化剂,该一锅反应被用于苯甲醛、5,5-二甲基-1,3-环己二酮和二氰基甲烷的缩合反应。催化剂负载量为 10 摩尔%、水和乙醇(1:1, v/v)混合溶剂、温度保持在 100°C 下 180 分钟时,反应达到最佳条件。制备出的苯并吡喃-5(6H)-酮衍生物谱系广泛,结果中等至良好。该方法的显著特点包括底物易得、反应时间短、使用环保溶剂,以及在分离产物时无需使用色谱法。在 2-氨基-3-氰基-4-苯基-7,7-二甲基-7,8-二氢-4H-1-苯并吡喃-5(6H)-酮的合成过程中,成功合成了一种新的酸性吡啶基离子液体,并将其用作催化剂。这些反应涉及芳香族苯甲醛、5,5-二甲基-1,3-环己二酮和二氰基甲烷在乙醇和水的混合溶剂中的缩合反应,以中等至良好的收率得到所需的产物。该方法既高效又环保,而且可以通过重结晶轻松获得产物。因此,该方法是现有方法的一种替代方案。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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
Preparation of pyridinium-based ionic liquid and application as a green catalyst for the synthetic route of 4H-1-benzopyran-5(6H)-ones
1-(4-sulfobutyl)pyridinium chlorozincate ionic liquid was synthesised in high yield (89%) through a simple route and characterised using FT-IR, NMR, and HRMS spectroscopy. The one-pot reaction was employed for the condensation reaction of benzaldehydes, 5,5-dimethyl-1,3-cyclohexanedione, and dicyanomethane, utilising the prepared ionic liquid catalyst. The optimal conditions for the reaction were achieved with a catalyst loading of 10 mol%, a solvent mixture of water and ethanol (1:1, v/v), maintained at 100°C for 180 minutes. A broad spectrum of benzopyran-5(6H)-one derivatives was prepared, yielding moderate to good results. The notable features of this procedure include readily available substrates, short reaction times, the use of environmentally friendly solvents, and the elimination of the need for chromatography in the isolation of products. Anew acidic pyridinium-based ionic liquid was successfully synthesised and used as a catalyst in the synthetic process of 2-amino-3-cyano-4-phenyl-7,7-dimethyl-7,8-dihydro-4H-1-benzopyran-5(6H)-ones. These reactions involved a condensation reaction of aromatic benzaldehydes, 5,5-dimethyl-1,3-cyclohexanedione, and dicyanomethane in a solvent mixture of ethanol and water, resulting in the desired products in moderate to good yields. The procedure is efficient and eco-friendly, and the products can be easily obtained by recrystallisation. Thus, this protocol offers an alternative to existing methods.
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
自引率
0.00%
发文量
0
期刊最新文献
Quantification of catalpol in root of Rehmannia glutinosa varieties 19 collected in Phu Tho province by high-performance liquid chromatography Morphology, anatomy, and quantitative determination of corosolic acid in Lagerstroemia calyculata Kurz in the Southeast region, Vietnam Prediction of geomechanical changes in faulted rock mass around underground structures subjected to earthquakes Synthesis of TiO2 by hydrothermal method using deep eutectic solvent for application in dye-sensitised solar cell Application of solid-phase extraction materials from ion liquids for the analysis of carbamate pesticide
×
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