• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

通过乌吉四中心三组分反应一步合成基于氧化吲哚的β-内酰胺。

One step access to oxindole-based β-lactams through Ugi four-center three-component reaction.

作者信息

Rainoldi Giulia, Lesma Giordano, Picozzi Claudia, Lo Presti Leonardo, Silvani Alessandra

机构信息

Dipartimento di Chimica, Università degli Studi di Milano Via Golgi 19 Milano, 20133 Italy

Department of Food, Environmental and Nutritional Sciences (DeFENS), Division of Food Microbiology and Bioprocessing Via Celoria 2 20133 Milan Italy.

出版信息

RSC Adv. 2018 Oct 11;8(61):34903-34910. doi: 10.1039/c8ra08165d. eCollection 2018 Oct 10.

DOI:10.1039/c8ra08165d
PMID:35547060
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9087354/
Abstract

A multicomponent Ugi reaction involving isatin, isocyanide and β-amino acid components has been developed. The reactions proceeded smoothly to give β-lactam-containing 3,3-disubstituted oxindoles in only one step and generally high yields. When chiral, non racemic, β-amino acids were used, products were obtained as enantiomerically pure β-lactams diastereoisomers, whose relative stereochemistry was determined by X-ray analysis. For one compound, a weak antibacterial activity has been preliminarily highlighted.

摘要

一种涉及异吲哚酮、异腈和β-氨基酸组分的多组分Ugi反应已被开发出来。反应顺利进行，仅一步即可得到含β-内酰胺的3,3-二取代氧化吲哚，且产率普遍较高。当使用手性、非外消旋的β-氨基酸时，产物以对映体纯的β-内酰胺非对映异构体形式获得，其相对立体化学通过X射线分析确定。对于一种化合物，已初步显示出较弱的抗菌活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/63bd322545bd/c8ra08165d-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/9f7b98136041/c8ra08165d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/6077c7fd7eff/c8ra08165d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/a20d9a9ed7cc/c8ra08165d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/fe85f3ec817a/c8ra08165d-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/e7b7a5cff9af/c8ra08165d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/dc2757040008/c8ra08165d-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/63bd322545bd/c8ra08165d-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/9f7b98136041/c8ra08165d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/6077c7fd7eff/c8ra08165d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/a20d9a9ed7cc/c8ra08165d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/fe85f3ec817a/c8ra08165d-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/e7b7a5cff9af/c8ra08165d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/dc2757040008/c8ra08165d-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3552/9087354/63bd322545bd/c8ra08165d-f4.jpg

相似文献

1
One step access to oxindole-based β-lactams through Ugi four-center three-component reaction.通过乌吉四中心三组分反应一步合成基于氧化吲哚的β-内酰胺。
RSC Adv. 2018 Oct 11;8(61):34903-34910. doi: 10.1039/c8ra08165d. eCollection 2018 Oct 10.
2
Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives.不对称 Ugi 3CR 在色胺衍生的亚胺上的反应：手性 3,3-二取代 3-氨基氧吲哚衍生物的合成。
Beilstein J Org Chem. 2014 Jun 18;10:1383-9. doi: 10.3762/bjoc.10.141. eCollection 2014.
3
Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence.甲基异腈作为一种可转化的官能团，用于通过一锅三步的序列，经Ugi-4CR后反应/转酰胺化/环化反应合成螺环氧化吲哚γ-内酰胺。
Beilstein J Org Chem. 2018 Apr 18;14:875-883. doi: 10.3762/bjoc.14.74. eCollection 2018.
4
Ugi Reaction Synthesis of Oxindole-Lactam Hybrids as Selective Butyrylcholinesterase Inhibitors.乌吉反应合成吲哚酮-内酰胺杂化物作为选择性丁酰胆碱酯酶抑制剂
ACS Med Chem Lett. 2021 Jul 23;12(11):1718-1725. doi: 10.1021/acsmedchemlett.1c00344. eCollection 2021 Nov 11.
5
Chiral pyrroline-based Ugi-three-component reactions are under kinetic control.手性吡咯烷为基础的 Ugi 三组分反应受动力学控制。
Org Lett. 2013 Jun 21;15(12):3026-9. doi: 10.1021/ol4012053. Epub 2013 May 30.
6
Still Unconquered: Enantioselective Passerini and Ugi Multicomponent Reactions.仍未攻克：对映选择性Passerini和Ugi多组分反应
Acc Chem Res. 2018 May 15;51(5):1290-1300. doi: 10.1021/acs.accounts.8b00105. Epub 2018 Apr 30.
7
Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles.连续的肼基-乌吉-叠氮化物反应：含1,5-二取代四唑的酰肼的合成
Beilstein J Org Chem. 2017 Dec 5;13:2596-2602. doi: 10.3762/bjoc.13.256. eCollection 2017.
8
Diversifying DNA-Tagged Amines by Isocyanide Multicomponent Reactions for DNA-Encoded Library Synthesis.通过异腈多组分反应实现DNA标记胺的多样化用于DNA编码文库合成
ACS Omega. 2024 Feb 7;9(7):7719-7724. doi: 10.1021/acsomega.3c07136. eCollection 2024 Feb 20.
9
Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations.基于吡咯基-β-氯代乙烯醛的乌吉双酰胺及其异常转化
Beilstein J Org Chem. 2024 Jul 26;20:1773-1784. doi: 10.3762/bjoc.20.156. eCollection 2024.
10
Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles.通过3,3-二取代氧化吲哚的催化对映选择性合成开发合成方法
Acc Chem Res. 2018 Jun 19;51(6):1443-1454. doi: 10.1021/acs.accounts.8b00097. Epub 2018 May 29.

引用本文的文献

1
Ugi Four-Component Reactions Using Alternative Reactants.Ugi 四组分反应中替代反应物的应用。
Molecules. 2023 Feb 8;28(4):1642. doi: 10.3390/molecules28041642.
2
Enantiopure β-isocyano-boronic esters: synthesis and exploitation in isocyanide-based multicomponent reactions.手性纯 β-异氰基硼酸酯：在基于异氰化物的多组分反应中的合成与应用。
Mol Divers. 2023 Oct;27(5):2161-2168. doi: 10.1007/s11030-022-10549-8. Epub 2022 Oct 19.
3
Ugi Reaction Synthesis of Oxindole-Lactam Hybrids as Selective Butyrylcholinesterase Inhibitors.乌吉反应合成吲哚酮-内酰胺杂化物作为选择性丁酰胆碱酯酶抑制剂

本文引用的文献

1
Sequential Multicomponent Strategy for the Diastereoselective Synthesis of Densely Functionalized Spirooxindole-Fused Thiazolidines.连续多组分策略用于非对映选择性合成稠合螺环氧化吲哚-噻唑烷。
ACS Comb Sci. 2018 Feb 12;20(2):98-105. doi: 10.1021/acscombsci.7b00179. Epub 2018 Jan 25.
2
Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids.3-酰基-2-氧化吲哚的催化脱酰基烷基化反应（DaA）的发展：中氧腊梅碱及相关生物碱的全合成
Chem Commun (Camb). 2017 Feb 9;53(13):2170-2173. doi: 10.1039/c6cc10228j.
3
Highly diastereoselective entry into chiral spirooxindole-based 4-methyleneazetidines via formal [2+2] annulation reaction.
ACS Med Chem Lett. 2021 Jul 23;12(11):1718-1725. doi: 10.1021/acsmedchemlett.1c00344. eCollection 2021 Nov 11.
通过形式上的[2+2]环化反应高度非对映选择性地合成基于手性螺环氧化吲哚的4-亚甲基氮杂环丁烷。
Chem Commun (Camb). 2016 Oct 4;52(77):11575-8. doi: 10.1039/c6cc05838h. Epub 2016 Sep 7.
4
Organocatalytic vinylogous Mannich reaction of trimethylsiloxyfuran with isatin-derived benzhydryl-ketimines.三甲基硅氧基呋喃与色酮衍生的苯甲叉基酮亚胺的有机催化反式 M an nich 反应。
Org Biomol Chem. 2016 Aug 10;14(32):7768-76. doi: 10.1039/c6ob01359g.
5
Organocatalytic Asymmetric Biginelli-like Reaction Involving Isatin.涉及异吲哚酮的有机催化不对称类Biginelli反应
J Org Chem. 2016 Mar 4;81(5):1877-84. doi: 10.1021/acs.joc.5b02680. Epub 2016 Feb 12.
6
Palladium(0)-catalyzed single and double isonitrile insertion: a facile synthesis of benzofurans, indoles, and isatins.钯（0）催化的单异腈和双异腈插入反应：苯并呋喃、吲哚和异吲哚酮的简便合成方法
Chemistry. 2015 Jan 12;21(3):998-1003. doi: 10.1002/chem.201405933. Epub 2014 Nov 28.
7
Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives.不对称 Ugi 3CR 在色胺衍生的亚胺上的反应：手性 3,3-二取代 3-氨基氧吲哚衍生物的合成。
Beilstein J Org Chem. 2014 Jun 18;10:1383-9. doi: 10.3762/bjoc.10.141. eCollection 2014.
8
Development of the EUCAST disk diffusion antimicrobial susceptibility testing method and its implementation in routine microbiology laboratories.EUCAST 纸片扩散法抗菌药物敏感性测试方法的制定及其在常规微生物学实验室中的应用。
Clin Microbiol Infect. 2014 Apr;20(4):O255-66. doi: 10.1111/1469-0691.12373. Epub 2013 Oct 17.
9
Synthesis of β-lactams by transition metal promoted Staudinger reactions: alternative synthetic approaches from transition metal enhanced organocatalysis to in situ, highly reactive intermediate synthesis and catalytic tandem reactions.过渡金属促进的 Staudinger 反应合成β-内酰胺：从过渡金属增强的有机催化到原位高反应性中间体合成和催化串联反应的替代合成方法。
Org Biomol Chem. 2013 Sep 28;11(36):5976-88. doi: 10.1039/c3ob41048j.
10
Recent approaches in design of peptidomimetics for antimicrobial drug discovery research.近年来用于抗菌药物发现研究的拟肽设计方法。
Mini Rev Med Chem. 2013 Jun;13(7):1073-88.