Metal-Free Synthesis of Functionalized Indolizines via a Cascade Michael/SN2/Aromatization Reaction of 2-Alkylazaarene Derivatives with Bromonitroolefins.
Kangbiao Chen, Rui Zhou, Gaofeng Zhu, Lei Tang, Lu Huang, Qing He
{"title":"Metal-Free Synthesis of Functionalized Indolizines via a Cascade Michael/S<sub>N</sub>2/Aromatization Reaction of 2-Alkylazaarene Derivatives with Bromonitroolefins.","authors":"Kangbiao Chen, Rui Zhou, Gaofeng Zhu, Lei Tang, Lu Huang, Qing He","doi":"10.1021/acsomega.4c09295","DOIUrl":null,"url":null,"abstract":"<p><p>A transition metal-free domino Michael/S<sub>N</sub>2/aromatization annulation of 2-pyridylacetates with bromonitroolefins has been developed. A wide range of substrates containing various substituted groups was compatible with the present methodology and afforded functionalized indolizines with moderate to excellent yield (up to 99% yield). In addition, the potential practicality of the method stood out through scale-up reactions and further transformations to other valuable compounds. In our view, this study is an essential complement for the rapid construction of indolizine derivatives through a metal-free strategy.</p>","PeriodicalId":22,"journal":{"name":"ACS Omega","volume":"9 50","pages":"49980-49985"},"PeriodicalIF":3.7000,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11656401/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Omega","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acsomega.4c09295","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/12/17 0:00:00","PubModel":"eCollection","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
A transition metal-free domino Michael/SN2/aromatization annulation of 2-pyridylacetates with bromonitroolefins has been developed. A wide range of substrates containing various substituted groups was compatible with the present methodology and afforded functionalized indolizines with moderate to excellent yield (up to 99% yield). In addition, the potential practicality of the method stood out through scale-up reactions and further transformations to other valuable compounds. In our view, this study is an essential complement for the rapid construction of indolizine derivatives through a metal-free strategy.
ACS OmegaChemical Engineering-General Chemical Engineering
CiteScore
6.60
自引率
4.90%
发文量
3945
审稿时长
2.4 months
期刊介绍:
ACS Omega is an open-access global publication for scientific articles that describe new findings in chemistry and interfacing areas of science, without any perceived evaluation of immediate impact.