4-亚肯唑与Arynes的区域选择性切换- alder反应构建萘[2,1-d]恶唑和1,4-环氧异喹啉

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC
Ying-Yi Wang, Feng Sha*, Yu-Hui Zheng and Xin-Yan Wu*, 
{"title":"4-亚肯唑与Arynes的区域选择性切换- alder反应构建萘[2,1-d]恶唑和1,4-环氧异喹啉","authors":"Ying-Yi Wang,&nbsp;Feng Sha*,&nbsp;Yu-Hui Zheng and Xin-Yan Wu*,&nbsp;","doi":"10.1021/acs.joc.4c0191910.1021/acs.joc.4c01919","DOIUrl":null,"url":null,"abstract":"<p >A Regioselectivity-switchable Diels–Alder reaction of arynes and 4-alkenyloxazoles was explored. By regulating the reaction temperature and the polarity of the solvent, the reaction activity of aryne was controlled to selectively react with different favorable reaction sites of 4-alkenyloxazoles, providing naphtho[2,1-<i>d</i>]oxazoles and 1,4-epoxyisoquinolines. Density functional theory (DFT) calculations demonstrated that the Diels–Alder reaction on acyclic dienes site needs more energy than the reaction on cyclic dienes to overcome the potential reaction barrier.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"89 23","pages":"17794–17803 17794–17803"},"PeriodicalIF":3.6000,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Construction of Naphtho[2,1-d]oxazoles and 1,4-Epoxyisoquinolines via Regioselectivity-Switchable Diels–Alder Reaction of 4-Alkenyloxazoles with Arynes\",\"authors\":\"Ying-Yi Wang,&nbsp;Feng Sha*,&nbsp;Yu-Hui Zheng and Xin-Yan Wu*,&nbsp;\",\"doi\":\"10.1021/acs.joc.4c0191910.1021/acs.joc.4c01919\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >A Regioselectivity-switchable Diels–Alder reaction of arynes and 4-alkenyloxazoles was explored. By regulating the reaction temperature and the polarity of the solvent, the reaction activity of aryne was controlled to selectively react with different favorable reaction sites of 4-alkenyloxazoles, providing naphtho[2,1-<i>d</i>]oxazoles and 1,4-epoxyisoquinolines. Density functional theory (DFT) calculations demonstrated that the Diels–Alder reaction on acyclic dienes site needs more energy than the reaction on cyclic dienes to overcome the potential reaction barrier.</p>\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"89 23\",\"pages\":\"17794–17803 17794–17803\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2024-11-13\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.joc.4c01919\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.4c01919","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

摘要

研究了芳香烃与4-烯氧氯唑的区域选择性可切换Diels-Alder反应。通过调节反应温度和溶剂极性,控制aryne的反应活性,选择性地与4-alkenyloxazoles的不同有利反应位点反应,得到萘[2,1-d]恶唑和1,4-环氧异喹啉。密度泛函理论(DFT)计算表明,非环二烯位上的Diels-Alder反应需要比环二烯位上的Diels-Alder反应需要更多的能量来克服反应势垒。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Construction of Naphtho[2,1-d]oxazoles and 1,4-Epoxyisoquinolines via Regioselectivity-Switchable Diels–Alder Reaction of 4-Alkenyloxazoles with Arynes

Construction of Naphtho[2,1-d]oxazoles and 1,4-Epoxyisoquinolines via Regioselectivity-Switchable Diels–Alder Reaction of 4-Alkenyloxazoles with Arynes

A Regioselectivity-switchable Diels–Alder reaction of arynes and 4-alkenyloxazoles was explored. By regulating the reaction temperature and the polarity of the solvent, the reaction activity of aryne was controlled to selectively react with different favorable reaction sites of 4-alkenyloxazoles, providing naphtho[2,1-d]oxazoles and 1,4-epoxyisoquinolines. Density functional theory (DFT) calculations demonstrated that the Diels–Alder reaction on acyclic dienes site needs more energy than the reaction on cyclic dienes to overcome the potential reaction barrier.

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
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
×
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