Unexpected one-pot synthesis of 3-cinnamoyl-3-hydroxyphthalide derivatives

Synlett Pub Date : 2024-04-23 DOI:10.1055/a-2312-0444
Intouch Rakchaya, Phanida Thongaram, Sengchan Saiyalard, Kredmanee Yimnoi, W. Wattanathana, Nutthawat Chuanopparat, P. Ngernmeesri
{"title":"Unexpected one-pot synthesis of 3-cinnamoyl-3-hydroxyphthalide derivatives","authors":"Intouch Rakchaya, Phanida Thongaram, Sengchan Saiyalard, Kredmanee Yimnoi, W. Wattanathana, Nutthawat Chuanopparat, P. Ngernmeesri","doi":"10.1055/a-2312-0444","DOIUrl":null,"url":null,"abstract":"A new and simple method to prepare 3-cinnamoyl-3-hydroxyphthalide derivatives from 2-hydroxy-3-methyl-1,4-naphthoquinone and substituted benzaldehydes was unexpectedly uncovered. The reaction was conveniently performed in DMSO at 100 ⁰C with K3PO4 as a base and AlCl3 as a catalyst. We proposed that the products occurred via a cascade process involving nucleophilic addition followed by demethylation and rearrangement. The products were typically obtained in moderate to good yields. The highest yield (95%) was obtained when the reaction of 2-bromobenzaldehyde was performed for 24 hours. X-ray crystallography of the product derived from 2-fluorobenzaldehyde unequivocally confirmed the structures of the hydroxyphthalide derivatives.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"87 10","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synlett","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2312-0444","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

Abstract

A new and simple method to prepare 3-cinnamoyl-3-hydroxyphthalide derivatives from 2-hydroxy-3-methyl-1,4-naphthoquinone and substituted benzaldehydes was unexpectedly uncovered. The reaction was conveniently performed in DMSO at 100 ⁰C with K3PO4 as a base and AlCl3 as a catalyst. We proposed that the products occurred via a cascade process involving nucleophilic addition followed by demethylation and rearrangement. The products were typically obtained in moderate to good yields. The highest yield (95%) was obtained when the reaction of 2-bromobenzaldehyde was performed for 24 hours. X-ray crystallography of the product derived from 2-fluorobenzaldehyde unequivocally confirmed the structures of the hydroxyphthalide derivatives.

Abstract Image

意想不到的 3-肉桂酰基-3-羟基苯酞衍生物的单锅合成
研究人员意外地发现了一种以 2-羟基-3-甲基-1,4-萘醌和取代的苯甲醛为原料制备 3-肉桂酰基-3-羟基苯酞衍生物的简便新方法。该反应以 K3PO4 为碱,AlCl3 为催化剂,在 DMSO 中于 100 ⁰C 温度下进行。我们认为,生成物是通过亲核加成、去甲基化和重排的级联过程产生的。这些产物的产率通常在中等到良好之间。当与 2-溴苯甲醛反应 24 小时后,产率最高(95%)。对 2-氟苯甲醛生成物的 X 射线晶体学研究明确证实了羟基苯酞衍生物的结构。
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
自引率
0.00%
发文量
0
×
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:604180095
Book学术官方微信