Isocyanoalkene Addition–Cyclization–Decarboxylation Cascades

Synthesis Pub Date : 2024-07-15 DOI:10.1055/s-0043-1774943
F. Fleming, John-Paul R Marrazzo, Tish Huynh
{"title":"Isocyanoalkene Addition–Cyclization–Decarboxylation Cascades","authors":"F. Fleming, John-Paul R Marrazzo, Tish Huynh","doi":"10.1055/s-0043-1774943","DOIUrl":null,"url":null,"abstract":"A rare conjugate addition to isocyanoalkenes with ethyl cyanoacetate triggers an efficient addition–cyclization–decarboxylation cascade. Using finely dispersed NaOH in THF as a base and nucleophile, is critical in facilitating the proton transfers, the ester hydrolysis, and the subsequent decarboxylation. The strategy provides an efficient route to valuable nitrile-substituted 2,3-dihydro-1H-pyrroles while providing fundamental insight into conjugate additions to isocyanoalkenes.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/s-0043-1774943","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 rare conjugate addition to isocyanoalkenes with ethyl cyanoacetate triggers an efficient addition–cyclization–decarboxylation cascade. Using finely dispersed NaOH in THF as a base and nucleophile, is critical in facilitating the proton transfers, the ester hydrolysis, and the subsequent decarboxylation. The strategy provides an efficient route to valuable nitrile-substituted 2,3-dihydro-1H-pyrroles while providing fundamental insight into conjugate additions to isocyanoalkenes.

Abstract Image

异氰基烯烃加成-环化-脱羧级联反应
异氰基烯烃与氰乙酸乙酯的罕见共轭加成引发了高效的加成-环化-脱羧级联反应。在四氢呋喃中使用精细分散的 NaOH 作为碱和亲核剂,对于促进质子转移、酯水解和随后的脱羧反应至关重要。该策略为获得有价值的腈取代 2,3-二氢-1H-吡咯提供了有效途径,同时也为异氰基烯烃的共轭加成提供了基本见解。
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:481959085
Book学术官方微信